SCS-C007428

tetrocarcin A

Pathway: Polyketides Superclass: Macrolides Class: Spirotetronate macrolides Glycoside

Chemical Structure

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Source Information

Micromonospora harpali (NA)

Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Micromonosporales Family Micromonosporaceae Genus Micromonospora Species Micromonospora haikouensis

South China Sea · -1565 m

DOI: 10.1021/acs.jnatprod.7b00176 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

1313.5 Da

Threshold ≤ 500

ALogP

6.36

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

3 violations (MW, ALogP, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C67H96N2O24

Molecular Weight:

1313.4950 Da

SMILES:

COC(=O)N[C@H]1[C@@H](C)O[C@@H](O[C@H]2C/C=C(\C)[C@@H]3C=C[C@@H]4[C@@H](O[C@H]5C[C@@H](O[C@H]6CC[C@@H](O[C@H]7C[C@@H](O)[C@@H](O[C@H]8CC[C@@H](O)[C@H](C)O8)[C@H](C)O7)[C@H](C)O6)[C@@H](OC(C)=O)[C@H](C)O5)[C@@H](C)C[C@H](C)[C@H]4[C@]3(C)C(=O)C3=C(O)[C@@]4(CC(C=O)=C[C@H](O)[C@H]4/C=C/2C)OC3=O)C[C@]1(C)[N+](=O)[O-]

InChIKey:

                        WMZWPJLTTUCZTC-TZZDMNFISA-N
                        
                    

InChI:

InChI=1S/C67H96N2O24/c1-30-14-18-47(88-54-28-65(11,69(79)80)60(38(9)86-54)68-64(78)81-13)31(2)23-43-45(73)24-40(29-70)27-67(43)62(76)55(63(77)93-67)61(75)66(12)42(30)16-15-41-56(66)32(3)22-33(4)57(41)92-53-26-49(59(37(8)85-53)87-39(10)71)90-50-21-19-48(35(6)83-50)89-52-25-46(74)58(36(7)84-52)91-51-20-17-44(72)34(5)82-51/h14-16,23-24,29,32-38,41-54,56-60,72-74,76H,17-22,25-28H2,1-13H3,(H,68,78)/b30-14+,31-23+/t32-,33-,34-,35-,36-,37-,38+,41-,42-,43+,44+,45-,46+,47-,48+,49+,50-,51-,52-,53-,54-,56+,57-,58-,59-,60-,65-,66+,67-/m0/s1

Calculated Properties

ALogP:

6.360 lipophilicity

TPSA:

341.43 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

10 (0 aromatic)

Chiral Centers:

Fsp³:

0.7761 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007428

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Macrolides

NPClassifier Class:

Spirotetronate macrolides

Glycoside:

Yes

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas

Biological Activity Data

Activity values are displayed only when a quantitative or clearly reported result is available. Tested organisms, cell lines and molecular targets are shown under Target / model.

Activity	Assay	Target / model	Result	Reference
Antibacterial	MIC	Bacillus subtilis BS01	0.016–0.5 μg/mL	10.1021/acs.jnatprod.7b00176 Journal of Natural Products
Antibacterial	MIC	Bacillus thuringiensis BT01	0.016–0.5 μg/mL	10.1021/acs.jnatprod.7b00176 Journal of Natural Products

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