NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	350.21
Volume:	364.849
LogP:	2.765
LogD:	2.551
LogS:	-3.357
# Rotatable Bonds:	3
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.779
Synthetic Accessibility Score:	4.921
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.774
MDCK Permeability:	1.9535817045834847e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.952
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.357
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.875
Plasma Protein Binding (PPB):	92.71812438964844%
Volume Distribution (VD):	1.234
Pgp-substrate:	13.012568473815918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.519
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.603
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.541
CYP3A4-inhibitor:	0.136
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	12.357
Half-life (T1/2):	0.754

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.956
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.189
Carcinogencity:	0.696
Eye Corrosion:	0.012
Eye Irritation:	0.039
Respiratory Toxicity:	0.971

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC477950

Natural Product ID:	NPC477950
*Common Name:**	3-[2-[(2S,3aS,5R,6R,8aS)-2,8a-dihydroxy-1,1,5,6-tetramethyl-4-oxo-2,3,3a,6,7,8-hexahydroazulen-5-yl]ethyl]-2H-furan-5-one
IUPAC Name:	3-[2-[(2S,3aS,5R,6R,8aS)-2,8a-dihydroxy-1,1,5,6-tetramethyl-4-oxo-2,3,3a,6,7,8-hexahydroazulen-5-yl]ethyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	XDKFKXXCPUQUEE-DBSYTYAISA-N
Standard InCHI:	InChI=1S/C20H30O5/c1-12-5-8-20(24)14(10-15(21)18(20,2)3)17(23)19(12,4)7-6-13-9-16(22)25-11-13/h9,12,14-15,21,24H,5-8,10-11H2,1-4H3/t12-,14-,15+,19-,20+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@H](C[C@@H](C2(C)C)O)C(=O)[C@]1(C)CCC3=CC(=O)OC3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90682204
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23559	Solidago shortii	Species	Asteraceae	Eukaryota	above-ground portion	Shaw Nature Reserve (Missouri Botanical Garden) (N 38 28.579, W 90 49.500)	2008-SEP	PMID[24922615]
NPO23559	Solidago shortii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	GI	=	56	%	PMID[24922615]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC477950 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	235
0.1-0.2	1409
0.2-0.3	5753
0.3-0.4	12169
0.4-0.5	11036
0.5-0.6	6520
0.6-0.7	4519
0.7-0.8	976
0.8-0.85	63
0.85-0.9	12
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9263	High Similarity	NPC477949
0.8788	High Similarity	NPC171759
0.866	High Similarity	NPC37408
0.8586	High Similarity	NPC141191
0.8571	High Similarity	NPC126156
0.8571	High Similarity	NPC185553
0.8529	High Similarity	NPC309190
0.8485	Intermediate Similarity	NPC169205
0.8485	Intermediate Similarity	NPC213947
0.8485	Intermediate Similarity	NPC108475
0.8485	Intermediate Similarity	NPC170143
0.8469	Intermediate Similarity	NPC48803
0.8469	Intermediate Similarity	NPC193645
0.8469	Intermediate Similarity	NPC275960
0.8469	Intermediate Similarity	NPC469873
0.8469	Intermediate Similarity	NPC90121
0.8416	Intermediate Similarity	NPC475099
0.8384	Intermediate Similarity	NPC142529
0.8384	Intermediate Similarity	NPC18019
0.8384	Intermediate Similarity	NPC91771
0.8384	Intermediate Similarity	NPC24956
0.8351	Intermediate Similarity	NPC284185
0.8333	Intermediate Similarity	NPC118405
0.8333	Intermediate Similarity	NPC212664
0.8333	Intermediate Similarity	NPC168679
0.8333	Intermediate Similarity	NPC12872
0.8317	Intermediate Similarity	NPC280963
0.83	Intermediate Similarity	NPC161493
0.8283	Intermediate Similarity	NPC476487
0.8283	Intermediate Similarity	NPC476488
0.8252	Intermediate Similarity	NPC110989
0.8247	Intermediate Similarity	NPC253144
0.82	Intermediate Similarity	NPC213078
0.8182	Intermediate Similarity	NPC167219
0.8173	Intermediate Similarity	NPC203659
0.8163	Intermediate Similarity	NPC150978
0.8163	Intermediate Similarity	NPC74103
0.8163	Intermediate Similarity	NPC70595
0.8163	Intermediate Similarity	NPC123177
0.8155	Intermediate Similarity	NPC225353
0.8144	Intermediate Similarity	NPC117405
0.8144	Intermediate Similarity	NPC52198
0.8137	Intermediate Similarity	NPC469872
0.8137	Intermediate Similarity	NPC469864
0.8125	Intermediate Similarity	NPC201658
0.8125	Intermediate Similarity	NPC45957
0.8125	Intermediate Similarity	NPC471657
0.8119	Intermediate Similarity	NPC69385
0.8119	Intermediate Similarity	NPC87090
0.8105	Intermediate Similarity	NPC245434
0.81	Intermediate Similarity	NPC52044
0.81	Intermediate Similarity	NPC213698
0.81	Intermediate Similarity	NPC67584
0.8095	Intermediate Similarity	NPC54737
0.8081	Intermediate Similarity	NPC153590
0.8081	Intermediate Similarity	NPC60386
0.8081	Intermediate Similarity	NPC473263
0.8081	Intermediate Similarity	NPC473234
0.8081	Intermediate Similarity	NPC473273
0.8081	Intermediate Similarity	NPC308656
0.8081	Intermediate Similarity	NPC200237
0.8058	Intermediate Similarity	NPC206079
0.8058	Intermediate Similarity	NPC477356
0.8058	Intermediate Similarity	NPC195192
0.8058	Intermediate Similarity	NPC304738
0.8039	Intermediate Similarity	NPC222011
0.8039	Intermediate Similarity	NPC477355
0.8039	Intermediate Similarity	NPC64742
0.8039	Intermediate Similarity	NPC470188
0.8021	Intermediate Similarity	NPC309757
0.8021	Intermediate Similarity	NPC236692
0.8021	Intermediate Similarity	NPC238593
0.802	Intermediate Similarity	NPC9812
0.8018	Intermediate Similarity	NPC475305
0.8	Intermediate Similarity	NPC100487
0.8	Intermediate Similarity	NPC127019
0.8	Intermediate Similarity	NPC96541
0.8	Intermediate Similarity	NPC477131
0.8	Intermediate Similarity	NPC144625
0.8	Intermediate Similarity	NPC469632
0.798	Intermediate Similarity	NPC221282
0.798	Intermediate Similarity	NPC171360
0.798	Intermediate Similarity	NPC133888
0.798	Intermediate Similarity	NPC35959
0.798	Intermediate Similarity	NPC286341
0.798	Intermediate Similarity	NPC57304
0.798	Intermediate Similarity	NPC261607
0.798	Intermediate Similarity	NPC29821
0.798	Intermediate Similarity	NPC293001
0.798	Intermediate Similarity	NPC475925
0.798	Intermediate Similarity	NPC191339
0.798	Intermediate Similarity	NPC111114
0.798	Intermediate Similarity	NPC63193
0.798	Intermediate Similarity	NPC300312
0.7963	Intermediate Similarity	NPC257240
0.7963	Intermediate Similarity	NPC477103
0.7959	Intermediate Similarity	NPC170775
0.7946	Intermediate Similarity	NPC475401
0.7941	Intermediate Similarity	NPC311904
0.7925	Intermediate Similarity	NPC243998
0.7925	Intermediate Similarity	NPC179891
0.7921	Intermediate Similarity	NPC170120
0.7921	Intermediate Similarity	NPC163228
0.7905	Intermediate Similarity	NPC475945
0.7905	Intermediate Similarity	NPC475871
0.79	Intermediate Similarity	NPC135776
0.79	Intermediate Similarity	NPC37816
0.79	Intermediate Similarity	NPC125180
0.789	Intermediate Similarity	NPC474750
0.789	Intermediate Similarity	NPC287311
0.7885	Intermediate Similarity	NPC150923
0.7885	Intermediate Similarity	NPC116139
0.7879	Intermediate Similarity	NPC129419
0.7879	Intermediate Similarity	NPC297474
0.7879	Intermediate Similarity	NPC77337
0.7879	Intermediate Similarity	NPC35809
0.7879	Intermediate Similarity	NPC216284
0.7879	Intermediate Similarity	NPC54065
0.7876	Intermediate Similarity	NPC477092
0.787	Intermediate Similarity	NPC477102
0.787	Intermediate Similarity	NPC139838
0.787	Intermediate Similarity	NPC59489
0.787	Intermediate Similarity	NPC475941
0.787	Intermediate Similarity	NPC474901
0.787	Intermediate Similarity	NPC47951
0.7864	Intermediate Similarity	NPC244411
0.7864	Intermediate Similarity	NPC54843
0.7864	Intermediate Similarity	NPC221615
0.785	Intermediate Similarity	NPC204884
0.785	Intermediate Similarity	NPC473911
0.7835	Intermediate Similarity	NPC70555
0.7835	Intermediate Similarity	NPC104961
0.7835	Intermediate Similarity	NPC70422
0.7822	Intermediate Similarity	NPC53685
0.7822	Intermediate Similarity	NPC470010
0.7822	Intermediate Similarity	NPC323008
0.7822	Intermediate Similarity	NPC198853
0.7822	Intermediate Similarity	NPC90453
0.7822	Intermediate Similarity	NPC262133
0.7822	Intermediate Similarity	NPC473331
0.7822	Intermediate Similarity	NPC470013
0.7822	Intermediate Similarity	NPC289004
0.7818	Intermediate Similarity	NPC123855
0.7818	Intermediate Similarity	NPC138757
0.7818	Intermediate Similarity	NPC76550
0.7812	Intermediate Similarity	NPC53011
0.7812	Intermediate Similarity	NPC37005
0.7812	Intermediate Similarity	NPC154893
0.7812	Intermediate Similarity	NPC16887
0.781	Intermediate Similarity	NPC105725
0.781	Intermediate Similarity	NPC474747
0.781	Intermediate Similarity	NPC66110
0.781	Intermediate Similarity	NPC49393
0.78	Intermediate Similarity	NPC131209
0.78	Intermediate Similarity	NPC184063
0.78	Intermediate Similarity	NPC290651
0.78	Intermediate Similarity	NPC472705
0.78	Intermediate Similarity	NPC133698
0.7798	Intermediate Similarity	NPC41551
0.7798	Intermediate Similarity	NPC206595
0.7798	Intermediate Similarity	NPC50223
0.7788	Intermediate Similarity	NPC161060
0.7778	Intermediate Similarity	NPC155935
0.7778	Intermediate Similarity	NPC215556
0.7778	Intermediate Similarity	NPC32922
0.7778	Intermediate Similarity	NPC308191
0.7778	Intermediate Similarity	NPC268298
0.7768	Intermediate Similarity	NPC72772
0.7768	Intermediate Similarity	NPC469794
0.7767	Intermediate Similarity	NPC471150
0.7759	Intermediate Similarity	NPC1538
0.7757	Intermediate Similarity	NPC190867
0.7757	Intermediate Similarity	NPC473488
0.7757	Intermediate Similarity	NPC475661
0.7757	Intermediate Similarity	NPC291643
0.7757	Intermediate Similarity	NPC223450
0.7755	Intermediate Similarity	NPC237540
0.7748	Intermediate Similarity	NPC209058
0.7748	Intermediate Similarity	NPC46269
0.7748	Intermediate Similarity	NPC106395
0.7748	Intermediate Similarity	NPC9848
0.7748	Intermediate Similarity	NPC312017
0.7745	Intermediate Similarity	NPC304886
0.7745	Intermediate Similarity	NPC476053
0.7745	Intermediate Similarity	NPC474490
0.7745	Intermediate Similarity	NPC472873
0.7739	Intermediate Similarity	NPC471999
0.7739	Intermediate Similarity	NPC472000
0.7736	Intermediate Similarity	NPC474775
0.7732	Intermediate Similarity	NPC78089
0.7731	Intermediate Similarity	NPC13071
0.7727	Intermediate Similarity	NPC475495
0.7723	Intermediate Similarity	NPC109414
0.7723	Intermediate Similarity	NPC477361
0.7723	Intermediate Similarity	NPC202824
0.7714	Intermediate Similarity	NPC133907
0.7714	Intermediate Similarity	NPC110443
0.7714	Intermediate Similarity	NPC46998
0.7714	Intermediate Similarity	NPC472753
0.7714	Intermediate Similarity	NPC62670

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC477950 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	2108
0.2-0.3	3859
0.3-0.4	2044
0.4-0.5	508
0.5-0.6	223
0.6-0.7	167
0.7-0.8	25
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8469	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5785	Approved
0.7963	Intermediate Similarity	NPD6371	Approved
0.7789	Intermediate Similarity	NPD6435	Approved
0.7685	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6053	Discontinued
0.7653	Intermediate Similarity	NPD5786	Approved
0.7579	Intermediate Similarity	NPD5368	Approved
0.7551	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5363	Approved
0.75	Intermediate Similarity	NPD5369	Approved
0.7455	Intermediate Similarity	NPD7320	Approved
0.7431	Intermediate Similarity	NPD6402	Approved
0.7431	Intermediate Similarity	NPD5739	Approved
0.7431	Intermediate Similarity	NPD6675	Approved
0.7431	Intermediate Similarity	NPD7128	Approved
0.7423	Intermediate Similarity	NPD4270	Approved
0.7423	Intermediate Similarity	NPD4269	Approved
0.7387	Intermediate Similarity	NPD6373	Approved
0.7387	Intermediate Similarity	NPD6372	Approved
0.7364	Intermediate Similarity	NPD5697	Approved
0.7364	Intermediate Similarity	NPD5701	Approved
0.7347	Intermediate Similarity	NPD5362	Discontinued
0.7297	Intermediate Similarity	NPD6899	Approved
0.7297	Intermediate Similarity	NPD6881	Approved
0.7264	Intermediate Similarity	NPD6084	Phase 2
0.7264	Intermediate Similarity	NPD6083	Phase 2
0.7257	Intermediate Similarity	NPD6650	Approved
0.7257	Intermediate Similarity	NPD6649	Approved
0.7255	Intermediate Similarity	NPD1695	Approved
0.7238	Intermediate Similarity	NPD5695	Phase 3
0.7232	Intermediate Similarity	NPD6014	Approved
0.7232	Intermediate Similarity	NPD6013	Approved
0.7232	Intermediate Similarity	NPD6012	Approved
0.7216	Intermediate Similarity	NPD4820	Approved
0.7216	Intermediate Similarity	NPD4819	Approved
0.7216	Intermediate Similarity	NPD4822	Approved
0.7216	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4252	Approved
0.7216	Intermediate Similarity	NPD4821	Approved
0.7196	Intermediate Similarity	NPD5696	Approved
0.7188	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7290	Approved
0.7168	Intermediate Similarity	NPD7102	Approved
0.7168	Intermediate Similarity	NPD6883	Approved
0.7154	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD6011	Approved
0.7105	Intermediate Similarity	NPD6869	Approved
0.7105	Intermediate Similarity	NPD6847	Approved
0.7105	Intermediate Similarity	NPD6617	Approved
0.7105	Intermediate Similarity	NPD8130	Phase 1
0.7103	Intermediate Similarity	NPD4755	Approved
0.7094	Intermediate Similarity	NPD7115	Discovery
0.7049	Intermediate Similarity	NPD7507	Approved
0.7043	Intermediate Similarity	NPD6882	Approved
0.7043	Intermediate Similarity	NPD8297	Approved
0.701	Intermediate Similarity	NPD4268	Approved
0.701	Intermediate Similarity	NPD4271	Approved
0.7	Intermediate Similarity	NPD5211	Phase 2
0.7	Intermediate Similarity	NPD7154	Phase 3
0.6981	Remote Similarity	NPD5282	Discontinued
0.6972	Remote Similarity	NPD5286	Approved
0.6972	Remote Similarity	NPD4700	Approved
0.6972	Remote Similarity	NPD5285	Approved
0.6972	Remote Similarity	NPD4696	Approved
0.6964	Remote Similarity	NPD6008	Approved
0.6961	Remote Similarity	NPD4249	Approved
0.6957	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5284	Approved
0.6952	Remote Similarity	NPD5281	Approved
0.6952	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD4753	Phase 2
0.6917	Remote Similarity	NPD6319	Approved
0.69	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5209	Approved
0.6893	Remote Similarity	NPD4251	Approved
0.6893	Remote Similarity	NPD4250	Approved
0.6887	Remote Similarity	NPD6399	Phase 3
0.6881	Remote Similarity	NPD4225	Approved
0.6881	Remote Similarity	NPD7638	Approved
0.6875	Remote Similarity	NPD5141	Approved
0.6864	Remote Similarity	NPD6274	Approved
0.6847	Remote Similarity	NPD4633	Approved
0.6847	Remote Similarity	NPD5226	Approved
0.6847	Remote Similarity	NPD5224	Approved
0.6847	Remote Similarity	NPD5225	Approved
0.6832	Remote Similarity	NPD5332	Approved
0.6832	Remote Similarity	NPD5331	Approved
0.6829	Remote Similarity	NPD7492	Approved
0.6827	Remote Similarity	NPD6903	Approved
0.6818	Remote Similarity	NPD7640	Approved
0.6818	Remote Similarity	NPD7639	Approved
0.68	Remote Similarity	NPD4790	Discontinued
0.6796	Remote Similarity	NPD7521	Approved
0.6796	Remote Similarity	NPD7334	Approved
0.6796	Remote Similarity	NPD7146	Approved
0.6796	Remote Similarity	NPD6684	Approved
0.6796	Remote Similarity	NPD6409	Approved
0.6796	Remote Similarity	NPD5330	Approved
0.6792	Remote Similarity	NPD6411	Approved
0.6786	Remote Similarity	NPD5175	Approved
0.6786	Remote Similarity	NPD5174	Approved
0.6777	Remote Similarity	NPD6059	Approved
0.6777	Remote Similarity	NPD6054	Approved
0.6774	Remote Similarity	NPD6616	Approved
0.6765	Remote Similarity	NPD3666	Approved
0.6765	Remote Similarity	NPD3665	Phase 1
0.6765	Remote Similarity	NPD3133	Approved
0.6759	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5210	Approved
0.6759	Remote Similarity	NPD4629	Approved
0.6757	Remote Similarity	NPD5223	Approved
0.6729	Remote Similarity	NPD5778	Approved
0.6729	Remote Similarity	NPD4202	Approved
0.6729	Remote Similarity	NPD5779	Approved
0.6724	Remote Similarity	NPD4634	Approved
0.6721	Remote Similarity	NPD6016	Approved
0.6721	Remote Similarity	NPD6015	Approved
0.6721	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8293	Discontinued
0.672	Remote Similarity	NPD7078	Approved
0.6699	Remote Similarity	NPD1694	Approved
0.6698	Remote Similarity	NPD46	Approved
0.6698	Remote Similarity	NPD5207	Approved
0.6698	Remote Similarity	NPD6698	Approved
0.6696	Remote Similarity	NPD6686	Approved
0.6695	Remote Similarity	NPD4632	Approved
0.6694	Remote Similarity	NPD7101	Approved
0.6694	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6637	Remote Similarity	NPD4754	Approved
0.6636	Remote Similarity	NPD7983	Approved
0.6636	Remote Similarity	NPD7637	Suspended
0.6612	Remote Similarity	NPD6314	Approved
0.6612	Remote Similarity	NPD6335	Approved
0.6612	Remote Similarity	NPD6313	Approved
0.6604	Remote Similarity	NPD6904	Approved
0.6604	Remote Similarity	NPD6673	Approved
0.6604	Remote Similarity	NPD6101	Approved
0.6604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6080	Approved
0.6604	Remote Similarity	NPD5328	Approved
0.6585	Remote Similarity	NPD6908	Approved
0.6585	Remote Similarity	NPD6909	Approved
0.6569	Remote Similarity	NPD4221	Approved
0.6569	Remote Similarity	NPD4223	Phase 3
0.6552	Remote Similarity	NPD4729	Approved
0.6552	Remote Similarity	NPD5128	Approved
0.6552	Remote Similarity	NPD4730	Approved
0.6545	Remote Similarity	NPD4697	Phase 3
0.6542	Remote Similarity	NPD5692	Phase 3
0.6529	Remote Similarity	NPD6009	Approved
0.6514	Remote Similarity	NPD6001	Approved
0.6509	Remote Similarity	NPD5208	Approved
0.6509	Remote Similarity	NPD6672	Approved
0.6509	Remote Similarity	NPD5737	Approved
0.6481	Remote Similarity	NPD6050	Approved
0.6481	Remote Similarity	NPD6079	Approved
0.6481	Remote Similarity	NPD5694	Approved
0.6476	Remote Similarity	NPD5279	Phase 3
0.6476	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD3618	Phase 1
0.6475	Remote Similarity	NPD7328	Approved
0.6475	Remote Similarity	NPD7327	Approved
0.6466	Remote Similarity	NPD6412	Phase 2
0.6452	Remote Similarity	NPD5983	Phase 2
0.6452	Remote Similarity	NPD8033	Approved
0.6449	Remote Similarity	NPD6051	Approved
0.6442	Remote Similarity	NPD4197	Approved
0.6441	Remote Similarity	NPD5251	Approved
0.6441	Remote Similarity	NPD5249	Phase 3
0.6441	Remote Similarity	NPD5250	Approved
0.6441	Remote Similarity	NPD5247	Approved
0.6441	Remote Similarity	NPD5248	Approved
0.6423	Remote Similarity	NPD7516	Approved
0.6408	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5222	Approved
0.6396	Remote Similarity	NPD5221	Approved
0.6396	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5215	Approved
0.6387	Remote Similarity	NPD5216	Approved
0.6387	Remote Similarity	NPD5217	Approved
0.6381	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5329	Approved
0.6371	Remote Similarity	NPD8294	Approved
0.6371	Remote Similarity	NPD8377	Approved
0.6356	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7604	Phase 2
0.6339	Remote Similarity	NPD5173	Approved
0.6339	Remote Similarity	NPD7902	Approved
0.6321	Remote Similarity	NPD4690	Approved
0.6321	Remote Similarity	NPD5690	Phase 2
0.6321	Remote Similarity	NPD4694	Approved
0.6321	Remote Similarity	NPD5205	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data