NPASS Natural Product

Natural Product: NPC70595

Natural Product ID:	NPC70595
Common Name:	Bigelovin
IUPAC Name:	[(3aS,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate
Synonyms:	6-O-Acetylmexicanin; Bigelovin
Molecular Formula:	C17H20O5
Standard InCHIKey:	DCNRYQODUSSOKC-MMLVVLEOSA-N
Standard InCHI:	InChI=1S/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11+,12+,14-,15+,17+/m1/s1
Canonical SMILES:	CC(=O)O[C@H]1[C@H]2[C@@H](OC(=O)C2=C)C[C@H]([C@H]2[C@@]1(C)C(=O)C=C2)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO12643	Delphinium dyctiocarpum	Species	Ranunculaceae	Eukaryota	UNPD*
NPO14825	Artemisia oliveriana	Species	Asteraceae	Eukaryota	UNPD*
NPO16576	Hopea chinensis	Species	Dipterocarpaceae	Eukaryota	UNPD*
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	UNPD*
NPO17312	Croomia heterosepala	Species	Stemonaceae	Eukaryota	UNPD*
NPO17529	Horsfieldia irya	Species	Myristicaceae	Eukaryota	UNPD*
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	UNPD*
NPO18092	Cleyera japonica	Species	Pentaphylacaceae	Eukaryota	UNPD*
NPO2282	Ageratina altissima	Species	Asteraceae	Eukaryota	UNPD*
NPO25921	Papaver nudicaule	Species	Papaveraceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
ED50	1
IC50	8
Others	3

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Others	7

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	900	nM	21894898
NPT2	Others	Unspecified		IC50	=	360	nM	9090867
NPT2	Others	Unspecified		IC50	=	2000	nM	9090867
NPT2	Others	Unspecified		Activity	=	67	%	23231968
NPT2	Others	Unspecified		Activity	=	74	%	23231968
NPT2	Others	Unspecified		Activity	=	76	%	23231968
NPT2	Others	Unspecified		IC50	=	2679.2	nM	23231968
NPT2	Others	Unspecified		IC50	=	946.2	nM	23231968
NPT2257	Cell Line	MCF-10A	Homo sapiens	IC50	=	26000	nM	24044895
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	ED50	=	4.9	nM	24959987

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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 NPC70595 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	147
0.1-0.2	801
0.2-0.3	3376
0.3-0.4	6750
0.4-0.5	10228
0.5-0.6	5342
0.6-0.7	3316
0.7-0.8	832
0.8-0.85	60
0.85-0.9	17
0.9-0.95	15
0.95-1	5

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Similarity Score	Similarity Level	Natural Product ID
0.7717	Intermediate Similarity	NPC38569
0.7723	Intermediate Similarity	NPC149371
0.7723	Intermediate Similarity	NPC472754
0.7727	Intermediate Similarity	NPC141789
0.7727	Intermediate Similarity	NPC57744

Showing 1 to 5 of 200 entries

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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 NPC70595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1415
0.2-0.3	3750
0.3-0.4	2548
0.4-0.5	838
0.5-0.6	285
0.6-0.7	154
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5862	Remote Similarity	NPD4730	Approved
0.5862	Remote Similarity	NPD4729	Approved
0.5865	Remote Similarity	NPD6098	Approved
0.5865	Remote Similarity	NPD4519	Discontinued
0.5865	Remote Similarity	NPD5279	Phase 3

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Structure

CID70595 OpenBabel06191715412D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.9312 1.5294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2596 -2.4705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6975 -4.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9511 -1.1703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0694 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4467 -0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5547 0.6645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5147 0.6645 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3456 -1.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6975 -3.3585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1132 -0.0861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9561 -0.0861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7237 -1.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1698 -1.0220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0347 -1.4385 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3773 -0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8996 -1.0220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5288 -2.8785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8098 -2.4705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3132 -1.0964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0347 -2.3985 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 9 2 0 0 0 0 3 10 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 8 1 1 6 0 0 0 8 11 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 17 1 1 0 0 0 12 7 1 6 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 15 17 1 6 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 4 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	3080597
ChEMBL	CHEMBL486997
ZINC

Physicochemical Properties

Molecular Weight:	304.13
ALogP:	0.5603
MLogP:	2.78
XLogP:	1.291
# Rotatable Bonds:	5
Polar Surface Area:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	22

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