Swietephragmin B - Compound Card

Swietephragmin B

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Swietephragmin B

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)C[C@H]1[C@@]2(C)C[C@]3([C@]1(C)C14CC[C@@]5(C(=CC(=O)O[C@H]5c5ccoc5)C54[C@@H](C3([C@H]2OC(=O)/C(=C/C)/C)OC(=O)C)OC(O1)(O5)C(CC)C)C)O
InChI InChI=1S/C39H48O13/c1-10-20(3)29(43)48-30-33(7)19-35(44)34(8,24(33)16-26(41)45-9)36-14-13-32(6)25(17-27(42)47-28(32)23-12-15-46-18-23)37(36)31(38(30,35)49-22(5)40)50-39(51-36,52-37)21(4)11-2/h10,12,15,17-18,21,24,28,30-31,44H,11,13-14,16,19H2,1-9H3/b20-10+/t21?,24-,28-,30-,31-,32+,33+,34+,35+,36?,37?,38?,39?/m0/s1
InChIKey HOKJOPUNHSFUMB-QVNUJKFWSA-N
Formula C39H48O13
HBA 13
HBD 1
MW 724.8
Rotatable Bonds 8
TPSA 166.26
LogP 4.76
Number Rings 8
Number Aromatic Rings 1
Heavy Atom Count 52
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 724.31
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: 101396720

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 724.8 g/mol

Structure

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

Level: 0

Mol. Weight: 724.8 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 724.8 g/mol

Antifeedant

Absorption

Caco-2 (logPapp)
-5.29
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
2.010
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
939.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.490
Plasma Protein Binding
92.19
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
7.110
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-21.980
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.100
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.660
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
-1708455.070
Rat (Acute)
4.710
Rat (Chronic Oral)
2.580
Fathead Minnow
2162.520
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
188229.480
Hydration Free Energy
-2.920
Log(D) at pH=7.4
3.660
Log(P)
4.41
Log S
-5.92
Log(Vapor Pressure)
-6175.72
Melting Point
228.63
pKa Acid
-17.53
pKa Basic
1.72
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 0.7599
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7599
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7366
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7366
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7355
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7355

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