NPASS Compound

Structure

NPC166857 OpenBabel07101718312D 26 28 0 0 1 0 0 0 0 0999 V2000 3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0491 -0.9430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0878 1.7891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 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 1 15 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 18 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 24 2 0 0 0 0 15 25 1 0 0 0 0 17 16 1 6 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 6 0 0 0 19 21 1 6 0 0 0 19 22 1 0 0 0 0 21 4 1 6 0 0 0 22 5 1 6 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.26
Volume:	393.287
LogP:	3.742
LogD:	3.42
LogS:	-4.035
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.598
Synthetic Accessibility Score:	4.554
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.66
MDCK Permeability:	2.6321578843635507e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.73
Plasma Protein Binding (PPB):	58.371543884277344%
Volume Distribution (VD):	1.326
Pgp-substrate:	41.46614456176758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.114
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.226
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.352

ADMET: Excretion

Clearance (CL):	6.271
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.236
AMES Toxicity:	0.636
Rat Oral Acute Toxicity:	0.426
Maximum Recommended Daily Dose:	0.703
Skin Sensitization:	0.868
Carcinogencity:	0.785
Eye Corrosion:	0.919
Eye Irritation:	0.736
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC166857

Natural Product ID:	NPC166857
*Common Name:**	FGEVYIKISBOJQP-BSFHOQSUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FGEVYIKISBOJQP-BSFHOQSUSA-N
Standard InCHI:	InChI=1S/C22H36O4/c1-15(24)25-14-16(8-12-23)17-13-19-21(4)10-6-9-20(2,3)18(21)7-11-22(19,5)26-17/h8,17-19,23H,6-7,9-14H2,1-5H3/b16-8-/t17-,18-,19+,21-,22+/m0/s1
SMILES:	OC/C=C([C@@H]1C[C@H]2[C@@](O1)(C)CC[C@@H]1[C@]2(C)CCCC1(C)C)/COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594161
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO33325	silphium laciniatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26287548]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	10000.0	nM	PMID[491452]

☑ 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 NPC166857 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	156
0.1-0.2	1104
0.2-0.3	4178
0.3-0.4	11939
0.4-0.5	10470
0.5-0.6	6346
0.6-0.7	5891
0.7-0.8	2364
0.8-0.85	213
0.85-0.9	34
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9186	High Similarity	NPC78973
0.9146	High Similarity	NPC155521
0.8941	High Similarity	NPC131813
0.8824	High Similarity	NPC35933
0.881	High Similarity	NPC476927
0.8795	High Similarity	NPC170303
0.878	High Similarity	NPC242767
0.8778	High Similarity	NPC276110
0.8736	High Similarity	NPC93411
0.8721	High Similarity	NPC329692
0.8706	High Similarity	NPC306951
0.869	High Similarity	NPC256112
0.869	High Similarity	NPC2524
0.8667	High Similarity	NPC105490
0.8652	High Similarity	NPC329842
0.8652	High Similarity	NPC72845
0.8652	High Similarity	NPC177641
0.8636	High Similarity	NPC246028
0.8636	High Similarity	NPC170633
0.8605	High Similarity	NPC474013
0.8602	High Similarity	NPC38855
0.8588	High Similarity	NPC311070
0.8587	High Similarity	NPC210337
0.8571	High Similarity	NPC472441
0.8556	High Similarity	NPC7349
0.8556	High Similarity	NPC472812
0.8556	High Similarity	NPC53555
0.8523	High Similarity	NPC106332
0.8506	High Similarity	NPC175145
0.8506	High Similarity	NPC475069
0.8495	Intermediate Similarity	NPC278673
0.8495	Intermediate Similarity	NPC275086
0.8495	Intermediate Similarity	NPC325229
0.8488	Intermediate Similarity	NPC102048
0.8488	Intermediate Similarity	NPC96055
0.8478	Intermediate Similarity	NPC88009
0.8462	Intermediate Similarity	NPC57117
0.8452	Intermediate Similarity	NPC281880
0.8452	Intermediate Similarity	NPC469802
0.8444	Intermediate Similarity	NPC472811
0.8427	Intermediate Similarity	NPC474396
0.8427	Intermediate Similarity	NPC20946
0.8427	Intermediate Similarity	NPC50488
0.8421	Intermediate Similarity	NPC109195
0.8421	Intermediate Similarity	NPC475038
0.8421	Intermediate Similarity	NPC472815
0.8409	Intermediate Similarity	NPC476948
0.8409	Intermediate Similarity	NPC131329
0.8404	Intermediate Similarity	NPC230546
0.8404	Intermediate Similarity	NPC324841
0.8404	Intermediate Similarity	NPC473510
0.8391	Intermediate Similarity	NPC476602
0.8387	Intermediate Similarity	NPC73911
0.8387	Intermediate Similarity	NPC51499
0.8372	Intermediate Similarity	NPC42476
0.8372	Intermediate Similarity	NPC23748
0.8372	Intermediate Similarity	NPC79945
0.837	Intermediate Similarity	NPC476720
0.8353	Intermediate Similarity	NPC25554
0.8353	Intermediate Similarity	NPC159148
0.8352	Intermediate Similarity	NPC152778
0.8352	Intermediate Similarity	NPC162615
0.8352	Intermediate Similarity	NPC205034
0.8352	Intermediate Similarity	NPC139692
0.8333	Intermediate Similarity	NPC473523
0.8333	Intermediate Similarity	NPC220216
0.8316	Intermediate Similarity	NPC11974
0.8316	Intermediate Similarity	NPC235142
0.8315	Intermediate Similarity	NPC472809
0.8315	Intermediate Similarity	NPC473879
0.8315	Intermediate Similarity	NPC472810
0.8298	Intermediate Similarity	NPC159763
0.8298	Intermediate Similarity	NPC278386
0.8298	Intermediate Similarity	NPC218107
0.8298	Intermediate Similarity	NPC124512
0.8295	Intermediate Similarity	NPC474970
0.828	Intermediate Similarity	NPC242848
0.828	Intermediate Similarity	NPC134072
0.828	Intermediate Similarity	NPC16967
0.828	Intermediate Similarity	NPC234993
0.8265	Intermediate Similarity	NPC475781
0.8261	Intermediate Similarity	NPC140277
0.8261	Intermediate Similarity	NPC469697
0.8256	Intermediate Similarity	NPC471218
0.8247	Intermediate Similarity	NPC473543
0.8242	Intermediate Similarity	NPC124374
0.8242	Intermediate Similarity	NPC234335
0.8229	Intermediate Similarity	NPC476081
0.8222	Intermediate Similarity	NPC82876
0.8222	Intermediate Similarity	NPC261320
0.8222	Intermediate Similarity	NPC473647
0.8222	Intermediate Similarity	NPC16265
0.8222	Intermediate Similarity	NPC470734
0.8211	Intermediate Similarity	NPC477971
0.8211	Intermediate Similarity	NPC228251
0.8211	Intermediate Similarity	NPC477968
0.8211	Intermediate Similarity	NPC251680
0.8211	Intermediate Similarity	NPC20113
0.8211	Intermediate Similarity	NPC477972
0.8211	Intermediate Similarity	NPC161527
0.8211	Intermediate Similarity	NPC219285
0.8202	Intermediate Similarity	NPC149224
0.8202	Intermediate Similarity	NPC245004
0.8191	Intermediate Similarity	NPC473244
0.8182	Intermediate Similarity	NPC164424
0.8182	Intermediate Similarity	NPC266511
0.8182	Intermediate Similarity	NPC38948
0.8171	Intermediate Similarity	NPC476366
0.8171	Intermediate Similarity	NPC201048
0.8161	Intermediate Similarity	NPC49208
0.8152	Intermediate Similarity	NPC38232
0.8152	Intermediate Similarity	NPC99653
0.8144	Intermediate Similarity	NPC189588
0.8144	Intermediate Similarity	NPC10232
0.8144	Intermediate Similarity	NPC97487
0.8144	Intermediate Similarity	NPC475526
0.8144	Intermediate Similarity	NPC187302
0.8144	Intermediate Similarity	NPC120321
0.8144	Intermediate Similarity	NPC329345
0.8144	Intermediate Similarity	NPC112009
0.8144	Intermediate Similarity	NPC297617
0.8144	Intermediate Similarity	NPC45897
0.8144	Intermediate Similarity	NPC120009
0.8144	Intermediate Similarity	NPC473283
0.8144	Intermediate Similarity	NPC196471
0.8144	Intermediate Similarity	NPC476237
0.814	Intermediate Similarity	NPC142163
0.8132	Intermediate Similarity	NPC221111
0.8132	Intermediate Similarity	NPC280149
0.8132	Intermediate Similarity	NPC476226
0.8132	Intermediate Similarity	NPC77796
0.8132	Intermediate Similarity	NPC182136
0.8132	Intermediate Similarity	NPC92885
0.8132	Intermediate Similarity	NPC209816
0.8132	Intermediate Similarity	NPC310479
0.8125	Intermediate Similarity	NPC247701
0.8125	Intermediate Similarity	NPC25177
0.8125	Intermediate Similarity	NPC471412
0.8125	Intermediate Similarity	NPC295110
0.8125	Intermediate Similarity	NPC475617
0.8125	Intermediate Similarity	NPC268829
0.8125	Intermediate Similarity	NPC222875
0.8111	Intermediate Similarity	NPC474629
0.8111	Intermediate Similarity	NPC104560
0.8105	Intermediate Similarity	NPC234617
0.8105	Intermediate Similarity	NPC124703
0.8105	Intermediate Similarity	NPC473154
0.81	Intermediate Similarity	NPC206618
0.8095	Intermediate Similarity	NPC283619
0.8095	Intermediate Similarity	NPC470711
0.8095	Intermediate Similarity	NPC132542
0.8095	Intermediate Similarity	NPC470758
0.809	Intermediate Similarity	NPC286153
0.809	Intermediate Similarity	NPC73038
0.8085	Intermediate Similarity	NPC276103
0.8085	Intermediate Similarity	NPC54248
0.8085	Intermediate Similarity	NPC471765
0.8085	Intermediate Similarity	NPC473153
0.8085	Intermediate Similarity	NPC475380
0.8085	Intermediate Similarity	NPC194132
0.8085	Intermediate Similarity	NPC190713
0.8085	Intermediate Similarity	NPC162346
0.8085	Intermediate Similarity	NPC221801
0.8085	Intermediate Similarity	NPC209297
0.8085	Intermediate Similarity	NPC211810
0.8085	Intermediate Similarity	NPC284194
0.8081	Intermediate Similarity	NPC475074
0.8081	Intermediate Similarity	NPC471205
0.8081	Intermediate Similarity	NPC475176
0.8081	Intermediate Similarity	NPC187435
0.8081	Intermediate Similarity	NPC301666
0.8081	Intermediate Similarity	NPC67321
0.8081	Intermediate Similarity	NPC131665
0.8081	Intermediate Similarity	NPC255387
0.8068	Intermediate Similarity	NPC470077
0.8065	Intermediate Similarity	NPC279410
0.8065	Intermediate Similarity	NPC474922
0.8065	Intermediate Similarity	NPC191521
0.8065	Intermediate Similarity	NPC201725
0.8065	Intermediate Similarity	NPC472360
0.8065	Intermediate Similarity	NPC470255
0.8065	Intermediate Similarity	NPC144202
0.8065	Intermediate Similarity	NPC119562
0.8065	Intermediate Similarity	NPC104925
0.8065	Intermediate Similarity	NPC298973
0.8065	Intermediate Similarity	NPC472416
0.8065	Intermediate Similarity	NPC91010
0.8046	Intermediate Similarity	NPC470049
0.8043	Intermediate Similarity	NPC249034
0.8043	Intermediate Similarity	NPC473675
0.8043	Intermediate Similarity	NPC49420
0.8043	Intermediate Similarity	NPC41239
0.8043	Intermediate Similarity	NPC477574
0.8041	Intermediate Similarity	NPC114540
0.8041	Intermediate Similarity	NPC238397
0.8041	Intermediate Similarity	NPC155332
0.8041	Intermediate Similarity	NPC475344
0.8041	Intermediate Similarity	NPC32577
0.8041	Intermediate Similarity	NPC476471
0.8041	Intermediate Similarity	NPC471363

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 NPC166857 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	1302
0.2-0.3	3915
0.3-0.4	2539
0.4-0.5	771
0.5-0.6	207
0.6-0.7	203
0.7-0.8	76
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8298	Intermediate Similarity	NPD4225	Approved
0.8211	Intermediate Similarity	NPD7640	Approved
0.8211	Intermediate Similarity	NPD7639	Approved
0.8105	Intermediate Similarity	NPD7638	Approved
0.7826	Intermediate Similarity	NPD6051	Approved
0.7614	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD7632	Discontinued
0.75	Intermediate Similarity	NPD7645	Phase 2
0.7444	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7115	Discovery
0.7363	Intermediate Similarity	NPD6695	Phase 3
0.732	Intermediate Similarity	NPD7748	Approved
0.7292	Intermediate Similarity	NPD7637	Suspended
0.7292	Intermediate Similarity	NPD7515	Phase 2
0.7283	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5739	Approved
0.7282	Intermediate Similarity	NPD6675	Approved
0.7282	Intermediate Similarity	NPD6402	Approved
0.7282	Intermediate Similarity	NPD7128	Approved
0.7228	Intermediate Similarity	NPD5344	Discontinued
0.7216	Intermediate Similarity	NPD6399	Phase 3
0.7204	Intermediate Similarity	NPD1694	Approved
0.7182	Intermediate Similarity	NPD7327	Approved
0.7182	Intermediate Similarity	NPD7328	Approved
0.7143	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD6899	Approved
0.7143	Intermediate Similarity	NPD6881	Approved
0.7129	Intermediate Similarity	NPD6648	Approved
0.7117	Intermediate Similarity	NPD7516	Approved
0.71	Intermediate Similarity	NPD6083	Phase 2
0.71	Intermediate Similarity	NPD7902	Approved
0.71	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6373	Approved
0.7075	Intermediate Similarity	NPD6372	Approved
0.7054	Intermediate Similarity	NPD8294	Approved
0.7054	Intermediate Similarity	NPD8377	Approved
0.7053	Intermediate Similarity	NPD7750	Discontinued
0.7053	Intermediate Similarity	NPD7524	Approved
0.7048	Intermediate Similarity	NPD5701	Approved
0.7048	Intermediate Similarity	NPD5697	Approved
0.7045	Intermediate Similarity	NPD7339	Approved
0.7045	Intermediate Similarity	NPD6942	Approved
0.7033	Intermediate Similarity	NPD6930	Phase 2
0.7033	Intermediate Similarity	NPD6931	Approved
0.7021	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6883	Approved
0.7009	Intermediate Similarity	NPD7102	Approved
0.7009	Intermediate Similarity	NPD7290	Approved
0.6991	Remote Similarity	NPD8033	Approved
0.6991	Remote Similarity	NPD8296	Approved
0.6991	Remote Similarity	NPD8380	Approved
0.6991	Remote Similarity	NPD8379	Approved
0.6991	Remote Similarity	NPD8335	Approved
0.6991	Remote Similarity	NPD8378	Approved
0.6981	Remote Similarity	NPD6686	Approved
0.697	Remote Similarity	NPD7900	Approved
0.697	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7334	Approved
0.6947	Remote Similarity	NPD6684	Approved
0.6947	Remote Similarity	NPD6409	Approved
0.6947	Remote Similarity	NPD7521	Approved
0.6947	Remote Similarity	NPD3618	Phase 1
0.6947	Remote Similarity	NPD5330	Approved
0.6947	Remote Similarity	NPD7146	Approved
0.6944	Remote Similarity	NPD6869	Approved
0.6944	Remote Similarity	NPD6649	Approved
0.6944	Remote Similarity	NPD6847	Approved
0.6944	Remote Similarity	NPD8130	Phase 1
0.6944	Remote Similarity	NPD6650	Approved
0.6944	Remote Similarity	NPD6617	Approved
0.6939	Remote Similarity	NPD8035	Phase 2
0.6939	Remote Similarity	NPD8034	Phase 2
0.6932	Remote Similarity	NPD6924	Approved
0.6932	Remote Similarity	NPD6926	Approved
0.6923	Remote Similarity	NPD6929	Approved
0.6916	Remote Similarity	NPD6013	Approved
0.6916	Remote Similarity	NPD6014	Approved
0.6916	Remote Similarity	NPD6012	Approved
0.6915	Remote Similarity	NPD4786	Approved
0.6907	Remote Similarity	NPD5328	Approved
0.69	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3667	Approved
0.6881	Remote Similarity	NPD8297	Approved
0.6881	Remote Similarity	NPD6882	Approved
0.6875	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5778	Approved
0.6869	Remote Similarity	NPD5779	Approved
0.6854	Remote Similarity	NPD8264	Approved
0.6852	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7514	Phase 3
0.6848	Remote Similarity	NPD7332	Phase 2
0.6842	Remote Similarity	NPD7503	Approved
0.6827	Remote Similarity	NPD5211	Phase 2
0.6822	Remote Similarity	NPD6011	Approved
0.6813	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6672	Approved
0.6804	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6903	Approved
0.6804	Remote Similarity	NPD5737	Approved
0.6789	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6933	Approved
0.6768	Remote Similarity	NPD6411	Approved
0.6768	Remote Similarity	NPD7087	Discontinued
0.6768	Remote Similarity	NPD6079	Approved
0.6768	Remote Similarity	NPD5693	Phase 1
0.6765	Remote Similarity	NPD4755	Approved
0.6752	Remote Similarity	NPD7507	Approved
0.6733	Remote Similarity	NPD5695	Phase 3
0.6729	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6925	Approved
0.6703	Remote Similarity	NPD5776	Phase 2
0.6701	Remote Similarity	NPD3573	Approved
0.67	Remote Similarity	NPD4202	Approved
0.6699	Remote Similarity	NPD5696	Approved
0.6698	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6008	Approved
0.6635	Remote Similarity	NPD4696	Approved
0.6635	Remote Similarity	NPD5285	Approved
0.6635	Remote Similarity	NPD5286	Approved
0.6635	Remote Similarity	NPD4700	Approved
0.6632	Remote Similarity	NPD7154	Phase 3
0.663	Remote Similarity	NPD7145	Approved
0.663	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6098	Approved
0.6596	Remote Similarity	NPD6898	Phase 1
0.6596	Remote Similarity	NPD6902	Approved
0.6588	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7319	Approved
0.6571	Remote Similarity	NPD4159	Approved
0.6566	Remote Similarity	NPD4753	Phase 2
0.6566	Remote Similarity	NPD6080	Approved
0.6566	Remote Similarity	NPD6904	Approved
0.6566	Remote Similarity	NPD6101	Approved
0.6566	Remote Similarity	NPD6673	Approved
0.6566	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3133	Approved
0.6562	Remote Similarity	NPD3666	Approved
0.6562	Remote Similarity	NPD3668	Phase 3
0.6562	Remote Similarity	NPD3665	Phase 1
0.6549	Remote Similarity	NPD6274	Approved
0.6522	Remote Similarity	NPD7101	Approved
0.6522	Remote Similarity	NPD6932	Approved
0.6522	Remote Similarity	NPD7100	Approved
0.6518	Remote Similarity	NPD8133	Approved
0.6517	Remote Similarity	NPD4243	Approved
0.6517	Remote Similarity	NPD7150	Approved
0.6517	Remote Similarity	NPD7151	Approved
0.6517	Remote Similarity	NPD7152	Approved
0.6509	Remote Similarity	NPD5226	Approved
0.6509	Remote Similarity	NPD5225	Approved
0.6509	Remote Similarity	NPD4633	Approved
0.6509	Remote Similarity	NPD5224	Approved
0.6505	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5221	Approved
0.6505	Remote Similarity	NPD5222	Approved
0.6505	Remote Similarity	NPD4697	Phase 3
0.65	Remote Similarity	NPD5785	Approved
0.6484	Remote Similarity	NPD8039	Approved
0.6477	Remote Similarity	NPD6923	Approved
0.6477	Remote Similarity	NPD6922	Approved
0.6471	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6001	Approved
0.6458	Remote Similarity	NPD5362	Discontinued
0.6452	Remote Similarity	NPD4268	Approved
0.6452	Remote Similarity	NPD4271	Approved
0.6449	Remote Similarity	NPD5174	Approved
0.6449	Remote Similarity	NPD5175	Approved
0.6442	Remote Similarity	NPD5173	Approved
0.6435	Remote Similarity	NPD6335	Approved
0.6429	Remote Similarity	NPD368	Approved
0.6429	Remote Similarity	NPD4623	Approved
0.6429	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD4519	Discontinued
0.6415	Remote Similarity	NPD5223	Approved
0.6413	Remote Similarity	NPD6117	Approved
0.641	Remote Similarity	NPD6909	Approved
0.641	Remote Similarity	NPD6908	Approved
0.6408	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7143	Approved
0.6404	Remote Similarity	NPD7144	Approved
0.6404	Remote Similarity	NPD6868	Approved
0.6387	Remote Similarity	NPD7492	Approved
0.6383	Remote Similarity	NPD4195	Approved
0.6383	Remote Similarity	NPD6683	Phase 2
0.6374	Remote Similarity	NPD4784	Approved
0.6374	Remote Similarity	NPD4785	Approved
0.6372	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD4250	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