NPASS Natural Product

Natural Product: NPC235402

Natural Product ID:	NPC235402
Common Name:	((1R,5S,6R,8S,8Ar)-8-Acetoxy-5-((2S,3As,5R,6Ar)-5-Hydroxyhexahydrofuro[2,3-B]Furan-2-Yl)-5,6-Dimethyloctahydro-2H-Spiro[Naphthalene-1,2'-Oxirane]-8A-Yl)Methyl Acetate
IUPAC Name:	[(4R,4aR,5S,7R,8S,8aR)-8-[(2S,3aS,5R,6aR)-5-hydroxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-5-acetyloxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
Synonyms:
Molecular Formula:	C24H36O8
Standard InCHIKey:	UXXDLTAQAXEQEL-MZVKURBCSA-N
Standard InCHI:	InChI=1S/C24H36O8/c1-13-8-19(30-15(3)26)24(12-28-14(2)25)17(6-5-7-23(24)11-29-23)22(13,4)18-9-16-10-20(27)32-21(16)31-18/h13,16-21,27H,5-12H2,1-4H3/t13-,16+,17-,18+,19+,20-,21-,22+,23+,24+/m1/s1
Canonical SMILES:	CC(=O)OC[C@@]12[C@@H](OC(=O)C)C[C@H]([C@]([C@H]1CCC[C@@]12CO1)(C)[C@@H]1C[C@@H]2[C@H](O1)O[C@H](C2)O)C
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
NPO3534	Ajuga lupulina	Species	Lamiaceae	Eukaryota				PMID[8759163]

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Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Organism	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	1.2	mm	3236005
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	1.2	mm	18597527

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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 NPC235402 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	219
0.1-0.2	2019
0.2-0.3	6003
0.3-0.4	10718
0.4-0.5	4642
0.5-0.6	4159
0.6-0.7	2583
0.7-0.8	484
0.8-0.85	40
0.85-0.9	19
0.9-0.95	2
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.75	Intermediate Similarity	NPC190940
0.75	Intermediate Similarity	NPC281004
0.75	Intermediate Similarity	NPC85593
0.75	Intermediate Similarity	NPC201607
0.75	Intermediate Similarity	NPC470062

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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 NPC235402 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	3269
0.2-0.3	3739
0.3-0.4	1167
0.4-0.5	391
0.5-0.6	253
0.6-0.7	68
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.56	Remote Similarity	NPD6695	Phase 3
0.5603	Remote Similarity	NPD8130	Phase 1
0.5603	Remote Similarity	NPD6617	Approved
0.5603	Remote Similarity	NPD6869	Approved
0.5603	Remote Similarity	NPD6847	Approved

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Structure

NPC235402 OpenBabel07101718222D 32 36 0 0 1 0 0 0 0 0999 V2000 -0.9730 3.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5549 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5549 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3021 3.2751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8156 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1304 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3605 1.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2112 1.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4865 -0.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7123 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9730 2.9189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5549 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5549 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2858 1.9459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8156 1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7886 2.4324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1304 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7831 2.4324 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2858 2.9189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8156 2.4324 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9730 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9730 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3975 -0.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3975 0.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7560 2.4324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7123 -0.9730 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 0.7123 0.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3605 3.2196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2112 3.2196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 17 1 0 0 0 0 7 23 1 0 0 0 0 8 13 1 0 0 0 0 8 19 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 11 29 1 0 0 0 0 12 28 1 0 0 0 0 13 22 1 6 0 0 0 14 25 2 0 0 0 0 14 28 1 0 0 0 0 15 26 2 0 0 0 0 15 30 1 0 0 0 0 16 9 1 1 0 0 0 16 21 1 0 0 0 0 17 22 1 6 0 0 0 17 24 1 0 0 0 0 18 9 1 6 0 0 0 18 22 1 0 0 0 0 18 31 1 0 0 0 0 19 24 1 6 0 0 0 19 30 1 0 0 0 0 20 27 1 6 0 0 0 20 32 1 0 0 0 0 21 31 1 1 0 0 0 21 32 1 0 0 0 0 22 4 1 6 0 0 0 23 24 1 1 0 0 0 23 29 1 0 0 0 0 24 12 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	44566824
ChEMBL	CHEMBL460553
ZINC

Physicochemical Properties

Molecular Weight:	452.24
ALogP:	-1.1379
MLogP:	3.22
XLogP:	2.916
# Rotatable Bonds:	11
Polar Surface Area:	103.82
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	32

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