Neomacrolactone - Compound Card

Neomacrolactone

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Neomacrolactone

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=O)O[C@H]1C[C@@]2([C@]([C@H]1[C@@H]([C@H](C(=O)C(=C)C(C)C)O)C)(C)CC[C@@]13C2CCC2[C@]3(C1)C=CC(=O)O[C@H]2C)C
InChI InChI=1S/C32H46O6/c1-17(2)18(3)27(35)28(36)19(4)26-23(38-21(6)33)15-30(8)24-10-9-22-20(5)37-25(34)11-12-31(22)16-32(24,31)14-13-29(26,30)7/h11-12,17,19-20,22-24,26,28,36H,3,9-10,13-16H2,1-2,4-8H3/t19-,20-,22?,23-,24?,26-,28+,29+,30-,31+,32-/m0/s1
InChIKey BMHBREVDFYUSCC-ZWFRJWGJSA-N
Formula C32H46O6
HBA 6
HBD 1
MW 526.71
Rotatable Bonds 6
TPSA 89.9
LogP 5.43
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 526.33
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Neoboutonia macrocalyx Euphorbiaceae Plantae 1260343

Showing of synonyms

  • Namukobe J, Kiremire BT, et al. (2014). Cycloartane triterpenes from the leaves of Neoboutonia macrocalyx L.. Phytochemistry,2014,102,189-196. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1=CC(=O)OCC(C1(C234)C2)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 526.71 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.88
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.8
Plasma Protein Binding
88.75
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
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
6.34
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.88
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.28
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.75
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1206.69
Rat (Acute)
3.14
Rat (Chronic Oral)
2.33
Fathead Minnow
6.11
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
473.61
Hydration Free Energy
-2.89
Log(D) at pH=7.4
4.73
Log(P)
3.92
Log S
-6.13
Log(Vapor Pressure)
-8.52
Melting Point
222.95
pKa Acid
8.98
pKa Basic
4.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8973
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8973
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8297
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8297
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7737
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7737
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7725
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7725
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7260
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7260
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7229
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7229

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