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

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

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4(13),7-coloratadiene-12,11-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]1CC=C1[C@@H]2COC1=O)C
InChI InChI=1S/C15H20O2/c1-9-6-7-15(3)12(10(9)2)5-4-11-13(15)8-17-14(11)16/h4,9,12-13H,2,5-8H2,1,3H3/t9-,12-,13-,15-/m0/s1
InChIKey CQWUYORFTUWURA-STAGSXQKSA-N
Formula C15H20O2
HBA 2
HBD 0
MW 232.32
Rotatable Bonds 0
TPSA 26.3
LogP 3.1
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 232.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Warburgia ugandensis Canellaceae Plantae 549619
2 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]
  • Wube AA, Bucar F, et al. (2005). Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. Phytochemistry,2005,66(19),2309-2315. [View] [PubMed]
Pubchem: 11651565
Nmrshiftdb2: 70009990

No compound-protein relationship available.

Structure

SMILES: C1CCC(=C)C(CC2)C1C(C=23)COC3=O

Level: 0

Mol. Weight: 232.32 g/mol

Antimycobacterial
Antitrypanosomal

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.65
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.0
Plasma Protein Binding
49.33
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.44
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.07
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.26
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
3.87
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
0.15
Rat (Acute)
2.09
Rat (Chronic Oral)
1.45
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
330.54
Hydration Free Energy
-3.17
Log(D) at pH=7.4
2.59
Log(P)
3.22
Log S
-4.61
Log(Vapor Pressure)
-4.11
Melting Point
101.55
pKa Acid
8.96
pKa Basic
6.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9237
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9237
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9123
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9123
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8893
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8893
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8702
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8702
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8692
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8692
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8574
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8574
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8543
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8543
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8498
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8498
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8390
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8390
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8308
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8308
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8299
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8299
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8285
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8285
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8264
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8264
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8191
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8191
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8034
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8034
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8013
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8013
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7803
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7803
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7756
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7756
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7745
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7745
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7653
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7653
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7651
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7651
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7602
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7602
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7521
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7521
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7491
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7491
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7416
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7416
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7402
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7402
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7375
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7375
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7356
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7356
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7352
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7352
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7347
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7347
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7341
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7341
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7216
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7216
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7215
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7215
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7196
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7196
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7187
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7187
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7154
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7154
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7127
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7127
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7121
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7121
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7112
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7112
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7093
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7093
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7091
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7091
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7085
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7085
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7070
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7070
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7067
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7067
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7059
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7059
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7051
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7051
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7050
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7050
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7029
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7029

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