3-ketotirucall-8,24-dien-21-oic acid - Compound Card

3-ketotirucall-8,24-dien-21-oic acid

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3-ketotirucall-8,24-dien-21-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=CCC([C@@H]1CCC2(C1CCC1=C2CCC2[C@]1(C)CCC(=O)C2(C)C)C)C(=O)O)C
InChI InChI=1S/C28H42O3/c1-17(2)7-8-19(25(30)31)18-13-15-27(5)20(18)9-10-22-21(27)11-12-23-26(3,4)24(29)14-16-28(22,23)6/h7,18-20,23H,8-16H2,1-6H3,(H,30,31)/t18-,19?,20?,23?,27?,28+/m0/s1
InChIKey DUXVLEPHSBFZLT-STUYUFFGSA-N
Formula C28H42O3
HBA 2
HBD 1
MW 426.64
Rotatable Bonds 4
TPSA 54.37
LogP 6.97
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 426.31
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Boswellia species Burseraceae Plantae 173701

Showing of synonyms

  • Melese A, Dagne E. (2007). Phytochemical investigation of the resins of Boswellia species collected from Kebtele area in Agew-Awi (Gojjam). M.Sc. Thesis, Addis Ababa University, Ethiopia, 2007. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3=C2CCC4C3CCC(=O)C4

Level: 0

Mol. Weight: 426.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.3
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.81
Plasma Protein Binding
85.35
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.95
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.01
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.44
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.93
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-36.69
Rat (Acute)
2.12
Rat (Chronic Oral)
2.17
Fathead Minnow
4.25
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
445.45
Hydration Free Energy
-4.37
Log(D) at pH=7.4
4.03
Log(P)
6.67
Log S
-5.89
Log(Vapor Pressure)
-7.71
Melting Point
178.7
pKa Acid
6.28
pKa Basic
7.44
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 0.8825
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8825
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8776
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8776
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8690
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8690
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8671
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8671
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8639
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8639
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8566
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8566
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8455
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8455
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8028
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8028
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7988
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7988
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7810
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7810
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7804
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7804
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7750
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7750
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7741
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7741
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7707
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7707
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7661
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7661
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7640
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7640
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7527
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7527
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7374
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7374
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7307
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7307
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7158
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7158
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7042
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7042
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7024
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7024

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