NPASS Natural Product

Natural Product: NPC471145

Natural Product ID:	NPC471145
Common Name:	Pungiolide A
IUPAC Name:	(3R,3aR,4'aR,5'S,6'aR,7R,8aS,9'aR,10'aR)-3'-acetyl-4'a-hydroxy-5',7-dimethyl-9'-methylidene-6-[(E)-3-oxobut-1-enyl]spiro[4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-3,2'-5,6,6a,9a,10,10a-hexahydrofuro[1,2]cyclohepta[5,7-d]pyran]-2,8'-dione
Synonyms:
Molecular Formula:	C29H34O8
Standard InCHIKey:	BGZGKGJBTWDZQU-PKNRYQKPSA-N
Standard InCHI:	InChI=1S/C29H34O8/c1-14-10-24-21(9-8-19(14)7-6-16(3)30)29(27(33)36-24)22(18(5)31)13-28(34)15(2)11-23-20(12-25(28)37-29)17(4)26(32)35-23/h6-8,13-15,20-21,23-25,34H,4,9-12H2,1-3,5H3/b7-6+/t14-,15+,20-,21-,23-,24+,25-,28+,29-/m1/s1
Canonical SMILES:	CC(=O)/C=C/C1=CC[C@@H]2[C@H](C[C@H]1C)OC(=O)[C@]12O[C@@H]2C[C@H]3[C@@H](C[C@@H]([C@]2(C=C1C(=O)C)O)C)OC(=O)C3=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
NPO32861	xanthium brasilicum	Species	Asteraceae	Eukaryota				PMID[23501116]

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Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Individual Protein	2
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	30000	nM	Open TG-GATES in vivo data: Biochemistry
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000	nM	22276851
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	18183025

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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 NPC471145 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	166
0.1-0.2	765
0.2-0.3	2679
0.3-0.4	5102
0.4-0.5	9794
0.5-0.6	8085
0.6-0.7	3313
0.7-0.8	932
0.8-0.85	41
0.85-0.9	11
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7623	Intermediate Similarity	NPC13710
0.7623	Intermediate Similarity	NPC475309
0.7623	Intermediate Similarity	NPC475401
0.7627	Intermediate Similarity	NPC115257
0.7627	Intermediate Similarity	NPC161816

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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 NPC471145 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1257
0.2-0.3	3362
0.3-0.4	2862
0.4-0.5	991
0.5-0.6	383
0.6-0.7	124
0.7-0.8	16
0.8-0.85	1
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
0.5703	Remote Similarity	NPD4633	Approved
0.5703	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD6190	Approved
0.5714	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8039	Approved

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Structure

NPC471145 OpenBabel07101719132D 37 41 0 0 1 0 0 0 0 0999 V2000 -2.5486 3.1986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3914 -3.0246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3714 5.5406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1349 1.5453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5027 4.2840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7773 3.6308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2080 2.0788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1934 1.1027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3390 1.5588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5603 -1.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6086 0.1205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9286 2.4445 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6086 -2.0729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2998 5.2389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2659 0.5779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9803 2.6760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5603 -0.0967 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9474 0.4827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9839 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9023 0.6857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1256 0.1153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7372 -0.8851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0252 5.8921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0051 0.5389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9402 -1.8400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3953 -0.6577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9512 -0.8452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 -0.1597 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 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 2 0 0 0 0 5 18 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 25 1 0 0 0 0 13 22 2 0 0 0 0 13 28 1 0 0 0 0 14 1 1 1 0 0 0 14 19 1 0 0 0 0 15 28 1 6 0 0 0 16 30 2 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 22 1 0 0 0 0 18 31 2 0 0 0 0 20 12 1 6 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 21 29 1 1 0 0 0 23 11 1 6 0 0 0 23 35 1 0 0 0 0 24 10 1 1 0 0 0 24 36 1 0 0 0 0 25 28 1 6 0 0 0 25 37 1 0 0 0 0 26 32 2 0 0 0 0 26 35 1 0 0 0 0 27 29 1 0 0 0 0 27 33 2 0 0 0 0 27 36 1 0 0 0 0 28 34 1 6 0 0 0 29 22 1 1 0 0 0 29 37 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	73348839
ChEMBL	CHEMBL2380790
ZINC

Physicochemical Properties

Molecular Weight:	510.23
ALogP:	-0.1242
MLogP:	3.77
XLogP:	1.704
# Rotatable Bonds:	8
Polar Surface Area:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	37

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