NPASS Natural Product

Natural Product: NPC170718

Natural Product ID:	NPC170718
Common Name:	Ferutinin
IUPAC Name:	[(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-hydroxybenzoate
Synonyms:	Ferutinin; Jaeschkeanadiol P-Hydroxybenzoate
Molecular Formula:	C22H30O4
Standard InCHIKey:	CYSHNJQMYORNJI-YUVXSKOASA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-14(2)22(25)12-11-21(4)10-9-15(3)13-18(19(21)22)26-20(24)16-5-7-17(23)8-6-16/h5-9,14,18-19,23,25H,10-13H2,1-4H3/t18-,19+,21-,22+/m0/s1
Canonical SMILES:	CC1=CC[C@@]2([C@@H]([C@H](C1)OC(=O)c1ccc(cc1)O)[C@](CC2)(O)C(C)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
NPO33190	ferula hermonis	Species	Apiaceae	Eukaryota				PMID[11277769]

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Biological Activity

Activity Type	# Activity
IC50	9
MIC	5
Others	9

Activity Type	# Activity
Cell Line	8
Individual Protein	6
Organism	7
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	10	%	26653328
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	0.5	%	18490506
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000	nM	9213587
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000	nM	10.6019/CHEMBL1201861
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	100000	nM	17685651
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	3.5	ug/ml	18809945
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	4	ug/ml	18809945
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000	nM	15745799
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	6.25	ug/ml	20350950
NPT2	Others	Unspecified		IC50	>	100000	nM	15104487

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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 NPC170718 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	203
0.1-0.2	910
0.2-0.3	1717
0.3-0.4	3685
0.4-0.5	7550
0.5-0.6	5806
0.6-0.7	7823
0.7-0.8	3095
0.8-0.85	91
0.85-0.9	5
0.9-0.95	4
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7808	Intermediate Similarity	NPC276652
0.7808	Intermediate Similarity	NPC301915
0.7808	Intermediate Similarity	NPC325805
0.7808	Intermediate Similarity	NPC187826
0.7808	Intermediate Similarity	NPC272523

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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 NPC170718 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	777
0.2-0.3	1436
0.3-0.4	2374
0.4-0.5	2260
0.5-0.6	1513
0.6-0.7	511
0.7-0.8	84
0.8-0.85	2
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
0.6686	Remote Similarity	NPD3818	Discontinued
0.6687	Remote Similarity	NPD3817	Phase 2
0.6687	Remote Similarity	NPD3226	Approved
0.6688	Remote Similarity	NPD5958	Discontinued
0.6688	Remote Similarity	NPD4534	Discontinued

Showing 1 to 5 of 200 entries

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Structure

NPC170718 OpenBabel07101718242D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.4790 0.6164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3291 -1.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4323 4.0515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0145 2.2124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1280 1.5093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2918 0.0610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 1.0265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1280 -0.4217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8071 2.9849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2898 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4928 0.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9137 -0.3121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8555 2.4721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9233 -0.1731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1477 3.1288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2918 1.0265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 0.0610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7833 1.5093 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0144 0.9654 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4556 1.5093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9371 1.2500 0.0000 C 0 0 2 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 -5.8003 -0.4217 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4556 2.4748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4059 -0.8761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6195 1.0265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 7 1 0 0 0 0 5 16 2 0 0 0 0 6 8 2 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 16 20 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 21 1 6 0 0 0 19 22 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 4 1 6 0 0 0 22 25 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	354654
ChEMBL	CHEMBL465040
ZINC

Physicochemical Properties

Molecular Weight:	358.21
ALogP:	1.0796
MLogP:	3.44
XLogP:	4.594
# Rotatable Bonds:	10
Polar Surface Area:	66.76
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	26

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