Swietephragmin C - Compound Card

Swietephragmin C

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Swietephragmin C

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)C[C@@H]1[C@]2(C)[C@@]3(C[C@@]1(C)[C@@H](C3(O)[C@@H]1C34C2(CC[C@@]2(C4=CC(=O)O[C@H]2c2ccoc2)C)OC(O3)(O1)C(CC)C)OC(=O)/C(=C/C)/C)O
InChI InChI=1S/C37H46O12/c1-9-19(3)27(40)46-28-31(6)18-33(41)32(7,22(31)15-24(38)43-8)34-13-12-30(5)23(16-25(39)45-26(30)21-11-14-44-17-21)36(34)29(35(28,33)42)47-37(48-34,49-36)20(4)10-2/h9,11,14,16-17,20,22,26,28-29,41-42H,10,12-13,15,18H2,1-8H3/b19-9+/t20?,22-,26-,28-,29+,30+,31+,32+,33+,34?,35?,36?,37?/m0/s1
InChIKey SPKRHHRYAOXOEE-FQBSLORXSA-N
Formula C37H46O12
HBA 12
HBD 2
MW 682.76
Rotatable Bonds 7
TPSA 160.19
LogP 4.19
Number Rings 8
Number Aromatic Rings 1
Heavy Atom Count 49
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 682.3
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Swietenia mahogani Meliaceae Plantae 459165

Showing of synonyms

  • Abdelgaleil SA, Doe M, et al. (2006). Rings B,D-seco limonoids from the leaves of Swietenia mahogani. Phytochemistry,2006,67(5),452-458. [View] [PubMed]
Pubchem: 101396721

No compound-protein relationship available.

Structure

SMILES: c1occc1C2OC(=O)C=C3C2CCC4(C356)C7C8C(C5OC(O6)O4)CC(C7)C8

Level: 1

Mol. Weight: 682.76 g/mol

Structure

SMILES: O1C(O2)OC3C(CC(C4)C5)C5C4C2(C136)CCC7C6=CC(=O)OC7

Level: 0

Mol. Weight: 682.76 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 682.76 g/mol

Antifeedant

Absorption

Caco-2 (logPapp)
-5.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.220
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
251.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.610
Plasma Protein Binding
91.28
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
5.880
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.890
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.380
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.200
Micronucleos
Toxic
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
-458230.510
Rat (Acute)
4.600
Rat (Chronic Oral)
2.800
Fathead Minnow
589.290
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
47403.420
Hydration Free Energy
-2.920
Log(D) at pH=7.4
3.700
Log(P)
4.24
Log S
-5.36
Log(Vapor Pressure)
-1559.93
Melting Point
226.71
pKa Acid
3.57
pKa Basic
2.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7538
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7538
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7320
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7320
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7230
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7230

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