SCS-C007429

tetrocarcin B

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

1199.4 Da

Threshold ≤ 500

ALogP

5.45

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:

C61H86N2O22

Molecular Weight:

1199.3510 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](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:

                        NVWJODYRCFLQNU-SHXCCBBDSA-N
                        
                    

InChI:

InChI=1S/C61H86N2O22/c1-27-13-16-42(81-48-25-59(10,63(73)74)54(34(8)79-48)62-58(72)75-12)28(2)20-39-40(66)21-36(26-64)24-61(39)56(70)49(57(71)85-61)55(69)60(11)38(27)15-14-37-50(60)29(3)19-30(4)52(37)84-47-23-44(53(33(7)78-47)80-35(9)65)83-45-18-17-43(31(5)76-45)82-46-22-41(67)51(68)32(6)77-46/h13-15,20-21,26,29-34,37-48,50-54,66-68,70H,16-19,22-25H2,1-12H3,(H,62,72)/b27-13+,28-20+/t29-,30-,31-,32-,33-,34+,37-,38-,39+,40-,41+,42-,43+,44+,45-,46-,47-,48-,50+,51-,52-,53-,54-,59-,60+,61-/m0/s1

Calculated Properties

ALogP:

5.450 lipophilicity

TPSA:

322.97 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

9 (0 aromatic)

Chiral Centers:

Fsp³:

0.7541 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007429

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, Bacillus thuringiensis BT01	0.016–0.5 μg/mL	10.1021/acs.jnatprod.7b00176 Journal of Natural Products

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