3,4-seco-lanosta-4(28),7,24-triene-3,21-dioic acid (13alpha,14beta,20s) - Compound Card

3,4-seco-lanosta-4(28),7,24-triene-3,21-dioic acid (13alpha,14beta,20s)

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3,4-seco-lanosta-4(28),7,24-triene-3,21-dioic acid (13alpha,14beta,20s)

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene Glycoside
Canonical Smiles COC(=O)CC[C@@]1(C)[C@@H](CC=C2[C@@H]1CC[C@@]1([C@]2(C)CC[C@@H]1C(C(=O)O)CCC=C(C)C)C)C(=C)C
InChI InChI=1S/C31H48O4/c1-20(2)10-9-11-22(28(33)34)24-14-18-31(7)26-13-12-23(21(3)4)29(5,17-16-27(32)35-8)25(26)15-19-30(24,31)6/h10,13,22-25H,3,9,11-12,14-19H2,1-2,4-8H3,(H,33,34)/t22?,23-,24+,25-,29-,30-,31+/m0/s1
InChIKey BDOYHNPLNKGOTP-JNLJXUBXSA-N
Formula C31H48O4
HBA 3
HBD 1
MW 484.72
Rotatable Bonds 9
TPSA 63.6
LogP 7.75
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 484.36
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pseudocedrela kotschyi Meliaceae Plantae 356281

Showing of synonyms

  • Sidjui LS, Nganso YOD, et al. (2018). Kostchyienones A and B, new antiplasmodial and cytotoxicity of limonoids from the roots of Pseudocedrela kotschyi (Schweinf.) Harms.. Zeitschrift fur Naturforschung. C, Journal of biosciences,2018, 73(3-4), 153-160. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2=CCCC3

Level: 0

Mol. Weight: 484.72 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.990
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.270
Plasma Protein Binding
98.34
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor

Excretion

Clearance
0.940
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.510
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.700
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
2.980
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
-174.730
Rat (Acute)
2.880
Rat (Chronic Oral)
1.970
Fathead Minnow
3.990
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
463.470
Hydration Free Energy
-2.910
Log(D) at pH=7.4
4.550
Log(P)
8.5
Log S
-6.2
Log(Vapor Pressure)
-9.19
Melting Point
146.8
pKa Acid
8.04
pKa Basic
6.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8783
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8501
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.8167
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8162
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8136
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8010
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7926
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7879
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7849
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7597
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7547
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7465
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7231
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7227
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7210
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7135
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7108
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7028
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7018
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7005

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