NPASS Natural Product

Natural Product: NPC99510

Natural Product ID:	NPC99510
Common Name:	7Alpha,10Alpha-Dihydroxy-1Beta-Methoxyeremophil-11(13)-En-12,8Beta-Olide
IUPAC Name:	(3aS,4aR,5S,8R,8aR,9aR)-3a,8a-dihydroxy-8-methoxy-4a,5-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one
Synonyms:
Molecular Formula:	C16H24O5
Standard InCHIKey:	BWYFZWWPWDWCAY-HFTAAXPDSA-N
Standard InCHI:	InChI=1S/C16H24O5/c1-9-5-6-11(20-4)16(19)7-12-15(18,8-14(9,16)3)10(2)13(17)21-12/h9,11-12,18-19H,2,5-8H2,1,3-4H3/t9-,11+,12+,14+,15-,16-/m0/s1
Canonical SMILES:	CO[C@@H]1CC[C@@H]([C@@]2([C@]1(O)C[C@H]1OC(=O)C(=C)[C@]1(C2)O)C)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
NPO33420	xylaria sp. bcc 21097	Species	Xylariaceae	Eukaryota				PMID[20155932]

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Biological Activity

Activity Type	# Activity
IC50	6
MIC	1

Activity Type	# Activity
Cell Line	4
Organism	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	3900	nM	23317013
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	169000	nM	17630726
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	8100	nM	PubChem BioAssay data set
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	3800	nM	17506585
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15000	nM	19928902
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	42000	nM	17630726
NPT91	Cell Line	KB	Homo sapiens	IC50	=	21000	nM	19928902

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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 NPC99510 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	159
0.1-0.2	1002
0.2-0.3	3008
0.3-0.4	4679
0.4-0.5	9754
0.5-0.6	5720
0.6-0.7	4657
0.7-0.8	1783
0.8-0.85	94
0.85-0.9	27
0.9-0.95	4
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.787	Intermediate Similarity	NPC471474
0.787	Intermediate Similarity	NPC112780
0.787	Intermediate Similarity	NPC67745
0.7876	Intermediate Similarity	NPC473590
0.7876	Intermediate Similarity	NPC473656

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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 NPC99510 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	1768
0.2-0.3	3516
0.3-0.4	2349
0.4-0.5	871
0.5-0.6	318
0.6-0.7	157
0.7-0.8	14
0.8-0.85	3
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
0.5888	Remote Similarity	NPD1780	Approved
0.5893	Remote Similarity	NPD4753	Phase 2
0.5902	Remote Similarity	NPD4729	Approved
0.5902	Remote Similarity	NPD5128	Approved
0.5902	Remote Similarity	NPD4730	Approved

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Structure

NPC99510 OpenBabel07101718232D 21 23 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2709 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 2 0 0 0 0 3 14 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 14 1 0 0 0 0 8 15 1 0 0 0 0 9 14 1 6 0 0 0 10 13 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 6 0 0 0 11 20 1 0 0 0 0 12 15 1 6 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 21 1 0 0 0 0 14 16 1 6 0 0 0 15 18 1 1 0 0 0 16 19 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	46211046
ChEMBL	CHEMBL1099250
ZINC

Physicochemical Properties

Molecular Weight:	296.16
ALogP:	-0.2722
MLogP:	2.67
XLogP:	0.968
# Rotatable Bonds:	6
Polar Surface Area:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	21

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