NPASS Natural Product

Natural Product: NPC228369

Natural Product ID:	NPC228369
Common Name:	Ent-Sandwicensin
IUPAC Name:	(6aS,11aS)-9-methoxy-10-(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol
Synonyms:
Molecular Formula:	C21H22O4
Standard InCHIKey:	ZFUZIYGRFSXEIQ-DYESRHJHSA-N
Standard InCHI:	InChI=1S/C21H22O4/c1-12(2)4-6-15-18(23-3)9-8-14-17-11-24-19-10-13(22)5-7-16(19)21(17)25-20(14)15/h4-5,7-10,17,21-22H,6,11H2,1-3H3/t17-,21-/m1/s1
Canonical SMILES:	COc1ccc2c(c1CC=C(C)C)O[C@H]1[C@@H]2COc2c1ccc(c2)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO27356	Erythrina glauca	Species	Fabaceae	Eukaryota				TCMID*
NPO33423	dalea formosa	Species	Fabaceae	Eukaryota	Root			PMID[23631483]

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Biological Activity

Activity Type	# Activity
MIC	6

Activity Type	# Activity
Organism	6

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	244	ug/ml	23631483
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	1.9	ug/ml	23631483
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	3.8	ug/ml	23631483
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	30.5	ug/ml	23631483
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	30.5	ug/ml	23631483

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Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC228369 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	1052
0.2-0.3	2097
0.3-0.4	5552
0.4-0.5	8014
0.5-0.6	2455
0.6-0.7	4999
0.7-0.8	4987
0.8-0.85	1134
0.85-0.9	246
0.9-0.95	63
0.95-1	54

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Similarity Score	Similarity Level	Natural Product ID
0.8741	High Similarity	NPC29799
0.8741	High Similarity	NPC209985
0.8741	High Similarity	NPC156502
0.8741	High Similarity	NPC306441
0.8741	High Similarity	NPC16435

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Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC228369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	843
0.2-0.3	1288
0.3-0.4	2534
0.4-0.5	2140
0.5-0.6	1117
0.6-0.7	748
0.7-0.8	237
0.8-0.85	14
0.85-0.9	5
0.9-0.95	3
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7114	Intermediate Similarity	NPD7030	Discontinued
0.7114	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6599	Discontinued
0.7122	Intermediate Similarity	NPD3705	Approved
0.7122	Intermediate Similarity	NPD1611	Approved

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Structure

CID228369 OpenBabel06191716022D 25 28 0 0 1 0 0 0 0 0999 V2000 0.6834 -3.3436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2858 -2.8233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0209 0.7221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0340 -1.6957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5284 -1.4585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6850 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6859 -0.9723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6856 1.9457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5278 1.4592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3704 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6853 1.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3344 -2.6209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3707 -0.9719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6857 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4598 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5276 0.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 0.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8424 0.4862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8427 0.4866 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2546 -1.4819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3699 -0.0006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5277 1.4602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 23 1 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 20 2 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 17 11 1 6 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 16 1 6 0 0 0 21 25 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	6993653
ChEMBL	CHEMBL2375518
ZINC

Physicochemical Properties

Molecular Weight:	338.15
ALogP:	0.7122
MLogP:	3.33
XLogP:	3.784
# Rotatable Bonds:	7
Polar Surface Area:	47.92
# H-Bond Aceptor:	0
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	25

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