15-O-methyllatrunculin B - Compound Card

15-O-methyllatrunculin B

Select a section from the left sidebar

15-O-methyllatrunculin B

Structure
Zoomed Structure
  • Family: Animalia - Podospongiidae
  • Kingdom: Animalia
  • Class: Polyketide
    • Subclass: Macrolide
Canonical Smiles CO[C@@]1(C[C@H]2C[C@H](O1)CC[C@H](C)/C=C\CC/C(=C\C(=O)O2)/C)[C@@H]1CSC(=O)N1
InChI InChI=1S/C21H31NO5S/c1-14-6-4-5-7-15(2)10-19(23)26-17-11-16(9-8-14)27-21(12-17,25-3)18-13-28-20(24)22-18/h4,6,10,14,16-18H,5,7-9,11-13H2,1-3H3,(H,22,24)/b6-4-,15-10-/t14-,16-,17-,18+,21-/m1/s1
InChIKey QFJACOUEVLILBV-TVVJMEDVSA-N
Formula C21H31NO5S
HBA 6
HBD 1
MW 409.55
Rotatable Bonds 2
TPSA 73.86
LogP 3.96
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 409.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Negombata magnifica Podospongiidae Animalia 344322

Showing of synonyms

  • El Sayed KA, Youssef DT, et al. (2006). Bioactive natural and semisynthetic latrunculins. Journal of Natural Products,2006,69(2),219-223. [View] [PubMed]
Pubchem: 14504505
Nmrshiftdb2: 60076534

No compound-protein relationship available.

Structure

SMILES: O=C1NC(CS1)C(CC23)OC(C2)CCCC=CCCC=CC(=O)O3

Level: 1

Mol. Weight: 409.55 g/mol

Structure

SMILES: C1COC(CC12)CCCC=CCCC=CC(=O)O2

Level: 0

Mol. Weight: 409.55 g/mol

Structure

SMILES: O=C1NCCS1

Level: 0

Mol. Weight: 409.55 g/mol

Anti-angiogenic
Antimicrobial

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.970
Plasma Protein Binding
54.69
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.210
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.920
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.110
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.270
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
-14.320
Rat (Acute)
2.400
Rat (Chronic Oral)
1.530
Fathead Minnow
3.930
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
444.510
Hydration Free Energy
-6.110
Log(D) at pH=7.4
3.210
Log(P)
3.23
Log S
-4.38
Log(Vapor Pressure)
-7.73
Melting Point
118.45
pKa Acid
9.0
pKa Basic
5.02
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 0.8322
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8322
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8259
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8259
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.8251
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.8251
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7470
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7470
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7335
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7335
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7202
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7202
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7062
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7062

Download SDF