6-hydroxyneomacolactone - Compound Card

6-hydroxyneomacolactone

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6-hydroxyneomacolactone

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@@]13C2C[C@@H](O)C2[C@]3(C1)C=CC(=O)O[C@H]2C)C
InChI InChI=1S/C32H46O7/c1-16(2)17(3)27(36)28(37)18(4)25-22(39-20(6)33)14-30(8)23-13-21(34)26-19(5)38-24(35)9-10-32(26)15-31(23,32)12-11-29(25,30)7/h9-10,16,18-19,21-23,25-26,28,34,37H,3,11-15H2,1-2,4-8H3/t18-,19-,21+,22-,23?,25-,26?,28+,29+,30-,31-,32+/m0/s1
InChIKey PFYLAAHFANZAGL-CQEQDISSSA-N
Formula C32H46O7
HBA 7
HBD 2
MW 542.71
Rotatable Bonds 6
TPSA 110.13
LogP 4.4
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 542.32
Number of Lipinski Rule Violations 1
# 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]
Pubchem: 86276185

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 542.71 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.29
Plasma Protein Binding
86.91
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
5.77
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.49
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.38
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.46
Micronucleos
Toxic
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
-1722.76
Rat (Acute)
4.2
Rat (Chronic Oral)
2.33
Fathead Minnow
7.04
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
458.26
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.9
Log(P)
3.18
Log S
-5.26
Log(Vapor Pressure)
-8.66
Melting Point
227.49
pKa Acid
7.83
pKa Basic
4.21
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 0.8743
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8743
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7982
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7982
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7389
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7389
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7267
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7267
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7220
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7211
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7211
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7199
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7199
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7134
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7134
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7069
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7069

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