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  3. 3-[[(1R,2R,4aR,6S,8aS)-2,6-dihydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-chloro-2,4-dihydroxy-6-methylbenzaldehyde

SCS-C001052

3-[[(1R,2R,4aR,6S,8aS)-2,6-dihydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-chloro-2,4-dihydroxy-6-methylbenzaldehyde

Pathway: Polyketides | Terpenoids Superclass: Meroterpenoids Class: Tetraketide meroterpenoids
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Chemical Structure

Structure of 3-[[(1R,2R,4aR,6S,8aS)-2,6-dihydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-chloro-2,4-dihydroxy-6-methylbenzaldehyde
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Download: SDF SMILES

Source Information

Acremonium sclerotigenum GXIMD 02501 (fungus)
Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Hypocreales Family Bionectriaceae Genus Acremonium Species Acremonium sclerotigenum
Weizhou Island  · 20°54′N, 109°06′E
DOI: 10.1021/acs.jmedchem.1c01402  · Journal of Medicinal Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight
425.0 Da
Threshold ≤ 500
ALogP
4.38
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C23H33ClO5
Molecular Weight:
424.9650 Da
SMILES:
Cc1c(Cl)c(O)c(C[C@@H]2[C@@]3(C)CC[C@H](O)C(C)(C)[C@@H]3CC[C@@]2(C)O)c(O)c1C=O
InChIKey:
DLZAYRRUNNMIQA-BPTKSNKRSA-N
InChI:
InChI=1S/C23H33ClO5/c1-12-14(11-25)19(27)13(20(28)18(12)24)10-16-22(4)8-7-17(26)21(2,3)15(22)6-9-23(16,5)29/h11,15-17,26-29H,6-10H2,1-5H3/t15-,16+,17-,22-,23+/m0/s1
Calculated Properties
ALogP:
4.379 lipophilicity
TPSA:
97.99 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
5
Rotatable Bonds:
3
Ring Count:
3 (1 aromatic)
Chiral Centers:
5
Fsp³:
0.6957 fraction sp³ carbon

Database Information

Compound ID:
SCS-C001052
NPClassifier Pathway:
Polyketides Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Tetraketide meroterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged