NPASS Natural Product

Natural Product: NPC475777

Natural Product ID:	NPC475777
Common Name:	1Alpha-Hydroxy-6Beta-(2Xi-Methylbutyryloxy)-10Alphah-9-Oxofuranoeremophilane
IUPAC Name:	[(4S,4aR,5S,8S,8aS)-8-hydroxy-3,4a,5-trimethyl-9-oxo-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-4-yl] 2-methylbutanoate
Synonyms:
Molecular Formula:	C20H28O5
Standard InCHIKey:	IAWIPMBPDIXBBM-ORSKTOQHSA-N
Standard InCHI:	InChI=1S/C20H28O5/c1-6-10(2)19(23)25-18-14-11(3)9-24-17(14)16(22)15-13(21)8-7-12(4)20(15,18)5/h9-10,12-13,15,18,21H,6-8H2,1-5H3/t10?,12-,13-,15-,18+,20+/m0/s1
Canonical SMILES:	CCC(C(=O)O[C@@H]1c2c(C)coc2C(=O)[C@H]2[C@@]1(C)[C@@H](C)CC[C@@H]2O)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
NPO28122	Senecio chionophilus	Species	Asteraceae	Eukaryota				PMID[15387646]

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Biological Activity

Activity Type	# Activity
MIC	1

Activity Type	# Activity
Organism	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	119	ug/ml	20189399

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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 NPC475777 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	237
0.1-0.2	996
0.2-0.3	2077
0.3-0.4	3849
0.4-0.5	7291
0.5-0.6	6514
0.6-0.7	5610
0.7-0.8	3996
0.8-0.85	224
0.85-0.9	84
0.9-0.95	10
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.821	Intermediate Similarity	NPC290400
0.821	Intermediate Similarity	NPC96443
0.821	Intermediate Similarity	NPC197596
0.821	Intermediate Similarity	NPC149896
0.8212	Intermediate Similarity	NPC202260

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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 NPC475777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	844
0.2-0.3	1765
0.3-0.4	2603
0.4-0.5	2138
0.5-0.6	1104
0.6-0.7	361
0.7-0.8	95
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6582	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7874	Approved
0.6584	Remote Similarity	NPD411	Approved
0.6584	Remote Similarity	NPD6410	Clinical (unspecified phase)

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Structure

NPC475777 OpenBabel07101718272D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.5053 4.3393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 3.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1832 2.1322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 1.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5053 3.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6702 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6702 -0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1541 -0.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6702 2.8929 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5873 0.2980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 0.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8351 -1.4464 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6702 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8351 -1.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6702 -0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 0.4821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6702 1.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8351 -2.4107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 -2.4107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5053 1.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -1.2623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 1.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 11 2 0 0 0 0 9 24 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 12 20 1 1 0 0 0 13 15 1 0 0 0 0 13 21 1 6 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 1 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 24 1 0 0 0 0 18 20 1 1 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	11290996
ChEMBL	CHEMBL515226
ZINC

Physicochemical Properties

Molecular Weight:	348.19
ALogP:	-0.1415
MLogP:	3.11
XLogP:	2.709
# Rotatable Bonds:	10
Polar Surface Area:	76.74
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	25

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