12beta-hydroxykulactone - Compound Card

12beta-hydroxykulactone

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12beta-hydroxykulactone

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=CCC[C@H]1C(=O)O[C@@H]2[C@@H]1[C@]1(C)[C@H](O)C[C@H]3C(=CC[C@@H]4[C@]3(C)CCC(=O)C4(C)C)[C@]1(C2)C)C
InChI InChI=1S/C30H44O4/c1-17(2)9-8-10-18-25-21(34-26(18)33)16-29(6)19-11-12-22-27(3,4)23(31)13-14-28(22,5)20(19)15-24(32)30(25,29)7/h9,11,18,20-22,24-25,32H,8,10,12-16H2,1-7H3/t18-,20+,21+,22+,24-,25-,28-,29-,30+/m1/s1
InChIKey UBPWASPNRWXDEI-UHJNRKMWSA-N
Formula C30H44O4
HBA 4
HBD 1
MW 468.68
Rotatable Bonds 3
TPSA 63.6
LogP 6.03
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 468.32
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Melia volkensii Meliaceae Plantae 643111

Showing of synonyms

  • Cantrell CL, Rajab MS, et al. (1999). Antimycobacterial triterpenes from Melia volkensii.. Journal of Natural Products,1999,62(4),546-548. [View] [PubMed]
Pubchem: 10367373
Nmrshiftdb2: 70016425

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC2CC(C3C12)C=4C(CC3)C5C(CC4)CC(=O)CC5

Level: 0

Mol. Weight: 468.68 g/mol

Antimycobacterial

Absorption

Caco-2 (logPapp)
-4.79
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
-1.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.81
Plasma Protein Binding
90.53
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
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
11.55
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.07
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.24
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.42
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-173.7
Rat (Acute)
2.04
Rat (Chronic Oral)
1.49
Fathead Minnow
3.92
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
498.83
Hydration Free Energy
-2.97
Log(D) at pH=7.4
5.16
Log(P)
5.61
Log S
-6.19
Log(Vapor Pressure)
-8.45
Melting Point
199.78
pKa Acid
9.71
pKa Basic
5.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8001
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8001
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7892
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7892
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7715
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7715
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7554
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7554
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7454
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7454
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7317
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7317
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7259
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7259
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7247
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7247
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7183
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7183
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7145
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7145
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7140
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7140
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7084
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7084

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