Isofouquierol - Compound Card

Isofouquierol

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Isofouquierol

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@H]2[C@](C/C=C/C(O)(C)C)(O)C)C)C
InChI InChI=1S/C30H52O3/c1-25(2,32)15-9-16-30(8,33)21-12-18-28(6)20(21)10-11-23-27(5)17-14-24(31)26(3,4)22(27)13-19-29(23,28)7/h9,15,20-24,31-33H,10-14,16-19H2,1-8H3/b15-9+/t20-,21+,22+,23-,24+,27+,28-,29-,30+/m1/s1
InChIKey ILQOLRWKVAXWJC-XVGAYARYSA-N
Formula C30H52O3
HBA 3
HBD 3
MW 460.74
Rotatable Bonds 4
TPSA 60.69
LogP 6.5
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 460.39
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Boswellia carterii Burseraceae Plantae 80276
2 Boswellia carterii Burseraceae Plantae 80276

Showing of synonyms

  • Yoshikawa M, Morikawa T, et al. (2009). Absolute stereostructures of olibanumols A, B, C, H, I, and J from olibanum, gum-resin of Boswellia carterii, and inhibitors of nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages. Chemical and Pharmaceutical Bulletin,2009,57(9),957-964. [View] [PubMed]
  • Morikawa T, Oominami H, et al. (2010). Four new ursane-type triterpenes, olibanumols K, L, M, and N, from Traditional Egyptian Medicine olibanum, the gum-resin of Boswellia carterii. Chemical and Pharmaceutical Bulletin,2010,58(11),1541-1544. [View] [PubMed]
Pubchem: 101974031
Nmrshiftdb2: 70017182

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 460.74 g/mol

Nitric oxide production inhibitory

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.15
Plasma Protein Binding
86.68
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
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.52
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.24
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.88
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.09
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
Toxic
T. Pyriformis
-63.47
Rat (Acute)
3.57
Rat (Chronic Oral)
1.63
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
410.73
Hydration Free Energy
-2.59
Log(D) at pH=7.4
5.93
Log(P)
6.24
Log S
-6.21
Log(Vapor Pressure)
-8.41
Melting Point
213.19
pKa Acid
11.28
pKa Basic
7.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8915
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8915
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8359
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8359
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8170
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8170
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7964
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7964
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7911
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7911
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7474
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7474
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7274
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7274
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7102
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7102
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7003
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7003

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