NPASS Compound

Structure

NPC475986 OpenBabel07101719512D 28 31 0 0 1 0 0 0 0 0999 V2000 1.4496 -0.7341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0890 -1.0045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6059 -0.1679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9537 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0105 -0.5989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0105 0.7925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2862 -0.5215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6804 -1.1518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4192 -0.8704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6129 -0.2510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6129 0.4446 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5920 -0.2510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2862 0.4446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5124 0.1376 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0932 1.0080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8141 -0.5300 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1229 -1.0045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1359 0.8784 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5920 0.4446 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9634 -0.0722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6438 -1.0796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1229 0.9277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4629 -0.0349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5510 1.8588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1229 -1.9706 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 1.4496 0.9277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1359 -0.6848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 11 1 0 0 0 0 6 19 1 0 0 0 0 7 13 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 20 1 0 0 0 0 9 26 1 0 0 0 0 10 11 1 0 0 0 0 11 27 1 6 0 0 0 12 19 1 1 0 0 0 12 28 1 0 0 0 0 13 22 2 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 6 0 0 0 15 18 1 1 0 0 0 15 24 1 0 0 0 0 16 20 1 1 0 0 0 16 28 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 6 0 0 0 19 8 1 6 0 0 0 20 18 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.19
Volume:	385.299
LogP:	0.89
LogD:	-0.141
LogS:	-3.371
# Rotatable Bonds:	5
TPSA:	128.98
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.288
Synthetic Accessibility Score:	6.316
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.653
MDCK Permeability:	0.00011059524695156142
Pgp-inhibitor:	0.002
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.226
20% Bioavailability (F20%):	0.489
30% Bioavailability (F30%):	0.331

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	28.531536102294922%
Volume Distribution (VD):	0.364
Pgp-substrate:	45.502586364746094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.688
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	4.055
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.513
Drug-inuced Liver Injury (DILI):	0.553
AMES Toxicity:	0.941
Rat Oral Acute Toxicity:	0.592
Maximum Recommended Daily Dose:	0.11
Skin Sensitization:	0.352
Carcinogencity:	0.143
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.303

Download Data

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

Natural Product: NPC475986

Natural Product ID:	NPC475986
*Common Name:**	FVUXHXRZJMFQJL-AXQZJTMXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FVUXHXRZJMFQJL-AXQZJTMXSA-N
Standard InCHI:	InChI=1S/C20H30O8/c1-10-5-12-19(8-21,6-11(10)27-13(22)7-17(2,3)25)18(4)15(24)14(23)16(28-12)20(18)9-26-20/h5,11-12,14-16,21,23-25H,6-9H2,1-4H3/t11-,12+,14+,15+,16+,18+,19+,20-/m0/s1
SMILES:	OC[C@]12C[C@H](OC(=O)CC(O)(C)C)C(=C[C@H]1O[C@H]1[C@]3([C@]2(C)[C@H](O)[C@H]1O)CO3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520531
PubChem CID:	44559328
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO15511	Fusarium heterosporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264681]
NPO15511	Fusarium heterosporum	Species	Nectriaceae	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
ED50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	ED50	>	1.28	ug	PMID[456405]

☑ 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 NPC475986 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	195
0.1-0.2	1260
0.2-0.3	4764
0.3-0.4	11912
0.4-0.5	10797
0.5-0.6	7163
0.6-0.7	5722
0.7-0.8	804
0.8-0.85	22
0.85-0.9	40
0.9-0.95	5
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC232515
0.9684	High Similarity	NPC26557
0.9681	High Similarity	NPC79449
0.9681	High Similarity	NPC474957
0.9583	High Similarity	NPC214714
0.9583	High Similarity	NPC200672
0.9583	High Similarity	NPC252242
0.9583	High Similarity	NPC475956
0.9574	High Similarity	NPC476057
0.9574	High Similarity	NPC347923
0.9485	High Similarity	NPC260809
0.9485	High Similarity	NPC474783
0.9474	High Similarity	NPC274458
0.9368	High Similarity	NPC182811
0.9362	High Similarity	NPC240838
0.898	High Similarity	NPC79631
0.875	High Similarity	NPC50223
0.8737	High Similarity	NPC197107
0.8725	High Similarity	NPC29389
0.8725	High Similarity	NPC469960
0.8725	High Similarity	NPC93026
0.8725	High Similarity	NPC265502
0.8641	High Similarity	NPC469959
0.8641	High Similarity	NPC472263
0.8641	High Similarity	NPC108682
0.8641	High Similarity	NPC469957
0.8598	High Similarity	NPC265290
0.8598	High Similarity	NPC305044
0.8585	High Similarity	NPC98038
0.8585	High Similarity	NPC313921
0.8571	High Similarity	NPC41551
0.8532	High Similarity	NPC474286
0.8532	High Similarity	NPC475130
0.8505	High Similarity	NPC101965
0.8505	High Similarity	NPC101400
0.8235	Intermediate Similarity	NPC98813
0.8235	Intermediate Similarity	NPC13743
0.8173	Intermediate Similarity	NPC123505
0.8165	Intermediate Similarity	NPC287075
0.8137	Intermediate Similarity	NPC65700
0.8095	Intermediate Similarity	NPC169843
0.8019	Intermediate Similarity	NPC470980
0.8019	Intermediate Similarity	NPC475290
0.7963	Intermediate Similarity	NPC77089
0.7961	Intermediate Similarity	NPC177232
0.7961	Intermediate Similarity	NPC212465
0.7925	Intermediate Similarity	NPC473577
0.7925	Intermediate Similarity	NPC475585
0.7925	Intermediate Similarity	NPC474550
0.7909	Intermediate Similarity	NPC126691
0.7818	Intermediate Similarity	NPC71680
0.7788	Intermediate Similarity	NPC222303
0.7778	Intermediate Similarity	NPC72813
0.7778	Intermediate Similarity	NPC474421
0.7778	Intermediate Similarity	NPC324327
0.7778	Intermediate Similarity	NPC194620
0.7778	Intermediate Similarity	NPC326994
0.7757	Intermediate Similarity	NPC181104
0.7757	Intermediate Similarity	NPC288502
0.7757	Intermediate Similarity	NPC103298
0.7757	Intermediate Similarity	NPC475335
0.7757	Intermediate Similarity	NPC201144
0.7757	Intermediate Similarity	NPC475331
0.7757	Intermediate Similarity	NPC80809
0.7757	Intermediate Similarity	NPC121518
0.7755	Intermediate Similarity	NPC477668
0.7748	Intermediate Similarity	NPC241477
0.7745	Intermediate Similarity	NPC281775
0.7739	Intermediate Similarity	NPC472004
0.7736	Intermediate Similarity	NPC470972
0.7727	Intermediate Similarity	NPC15551
0.7719	Intermediate Similarity	NPC475401
0.7706	Intermediate Similarity	NPC233379
0.7706	Intermediate Similarity	NPC474664
0.7706	Intermediate Similarity	NPC55972
0.7706	Intermediate Similarity	NPC327286
0.7706	Intermediate Similarity	NPC169888
0.7706	Intermediate Similarity	NPC14862
0.7699	Intermediate Similarity	NPC277583
0.7685	Intermediate Similarity	NPC9303
0.7685	Intermediate Similarity	NPC60315
0.7685	Intermediate Similarity	NPC16313
0.7664	Intermediate Similarity	NPC473523
0.7664	Intermediate Similarity	NPC69171
0.7664	Intermediate Similarity	NPC474165
0.7664	Intermediate Similarity	NPC474124
0.7664	Intermediate Similarity	NPC473694
0.7664	Intermediate Similarity	NPC475334
0.7664	Intermediate Similarity	NPC475623
0.7664	Intermediate Similarity	NPC4620
0.7658	Intermediate Similarity	NPC474750
0.7652	Intermediate Similarity	NPC477092
0.7642	Intermediate Similarity	NPC475617
0.7636	Intermediate Similarity	NPC475922
0.7636	Intermediate Similarity	NPC15218
0.7632	Intermediate Similarity	NPC475305
0.7629	Intermediate Similarity	NPC231601
0.7611	Intermediate Similarity	NPC216665
0.7611	Intermediate Similarity	NPC178289
0.7611	Intermediate Similarity	NPC106446
0.7607	Intermediate Similarity	NPC23786
0.7607	Intermediate Similarity	NPC107493
0.7607	Intermediate Similarity	NPC470265
0.7596	Intermediate Similarity	NPC113433
0.7596	Intermediate Similarity	NPC57664
0.7593	Intermediate Similarity	NPC220964
0.7593	Intermediate Similarity	NPC473543
0.7593	Intermediate Similarity	NPC475676
0.7593	Intermediate Similarity	NPC146731
0.7593	Intermediate Similarity	NPC296950
0.7589	Intermediate Similarity	NPC317687
0.7586	Intermediate Similarity	NPC79579
0.7576	Intermediate Similarity	NPC137253
0.757	Intermediate Similarity	NPC475344
0.757	Intermediate Similarity	NPC476471
0.757	Intermediate Similarity	NPC183571
0.757	Intermediate Similarity	NPC472552
0.7568	Intermediate Similarity	NPC472214
0.7568	Intermediate Similarity	NPC115257
0.7568	Intermediate Similarity	NPC161816
0.7568	Intermediate Similarity	NPC472215
0.7547	Intermediate Similarity	NPC230546
0.7545	Intermediate Similarity	NPC88701
0.7545	Intermediate Similarity	NPC94377
0.7544	Intermediate Similarity	NPC470075
0.7525	Intermediate Similarity	NPC299527
0.7524	Intermediate Similarity	NPC210337
0.7524	Intermediate Similarity	NPC205143
0.7523	Intermediate Similarity	NPC475802
0.7521	Intermediate Similarity	NPC471999
0.7521	Intermediate Similarity	NPC67569
0.7521	Intermediate Similarity	NPC472000
0.7521	Intermediate Similarity	NPC46570
0.75	Intermediate Similarity	NPC474775
0.75	Intermediate Similarity	NPC317107
0.75	Intermediate Similarity	NPC472821
0.75	Intermediate Similarity	NPC5292
0.75	Intermediate Similarity	NPC37603
0.75	Intermediate Similarity	NPC278681
0.75	Intermediate Similarity	NPC471786
0.7479	Intermediate Similarity	NPC8374
0.7478	Intermediate Similarity	NPC290693
0.7478	Intermediate Similarity	NPC203862
0.7478	Intermediate Similarity	NPC470171
0.7477	Intermediate Similarity	NPC11974
0.7477	Intermediate Similarity	NPC280991
0.7477	Intermediate Similarity	NPC472554
0.7477	Intermediate Similarity	NPC472216
0.7477	Intermediate Similarity	NPC187876
0.7477	Intermediate Similarity	NPC5475
0.7477	Intermediate Similarity	NPC173905
0.7477	Intermediate Similarity	NPC284828
0.7459	Intermediate Similarity	NPC173347
0.7458	Intermediate Similarity	NPC115349
0.7458	Intermediate Similarity	NPC269642
0.7456	Intermediate Similarity	NPC43213
0.7455	Intermediate Similarity	NPC475781
0.7451	Intermediate Similarity	NPC246173
0.7449	Intermediate Similarity	NPC477667
0.7438	Intermediate Similarity	NPC311534
0.7436	Intermediate Similarity	NPC112936
0.7436	Intermediate Similarity	NPC474370
0.7434	Intermediate Similarity	NPC473877
0.7431	Intermediate Similarity	NPC472822
0.7431	Intermediate Similarity	NPC152966
0.7431	Intermediate Similarity	NPC258532
0.7429	Intermediate Similarity	NPC170527
0.7429	Intermediate Similarity	NPC284063
0.7429	Intermediate Similarity	NPC88009
0.7419	Intermediate Similarity	NPC471234
0.7414	Intermediate Similarity	NPC288679
0.7414	Intermediate Similarity	NPC16701
0.7414	Intermediate Similarity	NPC13710
0.7414	Intermediate Similarity	NPC153440
0.7411	Intermediate Similarity	NPC235014
0.7407	Intermediate Similarity	NPC49393
0.7407	Intermediate Similarity	NPC475038
0.7407	Intermediate Similarity	NPC109195
0.7407	Intermediate Similarity	NPC474709
0.7404	Intermediate Similarity	NPC472467
0.74	Intermediate Similarity	NPC478112
0.7395	Intermediate Similarity	NPC469789
0.7391	Intermediate Similarity	NPC106228
0.7391	Intermediate Similarity	NPC138372
0.7391	Intermediate Similarity	NPC5311
0.7391	Intermediate Similarity	NPC193382
0.7391	Intermediate Similarity	NPC310341
0.7391	Intermediate Similarity	NPC199428
0.7391	Intermediate Similarity	NPC99620
0.7387	Intermediate Similarity	NPC135015
0.7387	Intermediate Similarity	NPC10150
0.7387	Intermediate Similarity	NPC217921
0.7387	Intermediate Similarity	NPC308191
0.7387	Intermediate Similarity	NPC128795
0.7387	Intermediate Similarity	NPC48548
0.7387	Intermediate Similarity	NPC117604
0.7387	Intermediate Similarity	NPC472825
0.7383	Intermediate Similarity	NPC79303
0.7383	Intermediate Similarity	NPC473510
0.7383	Intermediate Similarity	NPC280963

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 NPC475986 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1593
0.2-0.3	4023
0.3-0.4	2366
0.4-0.5	566
0.5-0.6	275
0.6-0.7	163
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7451	Intermediate Similarity	NPD6698	Approved
0.7451	Intermediate Similarity	NPD46	Approved
0.729	Intermediate Similarity	NPD7638	Approved
0.7288	Intermediate Similarity	NPD6319	Approved
0.7265	Intermediate Similarity	NPD7328	Approved
0.7265	Intermediate Similarity	NPD7327	Approved
0.7257	Intermediate Similarity	NPD6371	Approved
0.7236	Intermediate Similarity	NPD7319	Approved
0.7227	Intermediate Similarity	NPD7503	Approved
0.7227	Intermediate Similarity	NPD8033	Approved
0.7222	Intermediate Similarity	NPD7640	Approved
0.7222	Intermediate Similarity	NPD7639	Approved
0.7203	Intermediate Similarity	NPD7516	Approved
0.7179	Intermediate Similarity	NPD7115	Discovery
0.7168	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8294	Approved
0.7143	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8377	Approved
0.7131	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD4225	Approved
0.7115	Intermediate Similarity	NPD7838	Discovery
0.7083	Intermediate Similarity	NPD8335	Approved
0.7083	Intermediate Similarity	NPD8378	Approved
0.7083	Intermediate Similarity	NPD8380	Approved
0.7083	Intermediate Similarity	NPD8296	Approved
0.7083	Intermediate Similarity	NPD8379	Approved
0.708	Intermediate Similarity	NPD6686	Approved
0.6991	Remote Similarity	NPD6412	Phase 2
0.6983	Remote Similarity	NPD6053	Discontinued
0.6957	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4249	Approved
0.6887	Remote Similarity	NPD7637	Suspended
0.6847	Remote Similarity	NPD5344	Discontinued
0.6827	Remote Similarity	NPD4251	Approved
0.6827	Remote Similarity	NPD4250	Approved
0.6803	Remote Similarity	NPD8516	Approved
0.6803	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD8515	Approved
0.6803	Remote Similarity	NPD8517	Approved
0.68	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4819	Approved
0.68	Remote Similarity	NPD4822	Approved
0.68	Remote Similarity	NPD4820	Approved
0.68	Remote Similarity	NPD4821	Approved
0.6796	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4632	Approved
0.6774	Remote Similarity	NPD7492	Approved
0.6729	Remote Similarity	NPD7983	Approved
0.6721	Remote Similarity	NPD6054	Approved
0.6721	Remote Similarity	NPD6059	Approved
0.672	Remote Similarity	NPD6616	Approved
0.6698	Remote Similarity	NPD6051	Approved
0.6696	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6639	Remote Similarity	NPD8133	Approved
0.6638	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7632	Discontinued
0.6636	Remote Similarity	NPD5785	Approved
0.6614	Remote Similarity	NPD7736	Approved
0.6613	Remote Similarity	NPD6370	Approved
0.6613	Remote Similarity	NPD5988	Approved
0.661	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5739	Approved
0.6609	Remote Similarity	NPD6675	Approved
0.6609	Remote Similarity	NPD7128	Approved
0.6609	Remote Similarity	NPD6402	Approved
0.6609	Remote Similarity	NPD6008	Approved
0.66	Remote Similarity	NPD4268	Approved
0.66	Remote Similarity	NPD4271	Approved
0.6581	Remote Similarity	NPD6372	Approved
0.6581	Remote Similarity	NPD6373	Approved
0.6577	Remote Similarity	NPD6083	Phase 2
0.6577	Remote Similarity	NPD6084	Phase 2
0.6552	Remote Similarity	NPD5701	Approved
0.6552	Remote Similarity	NPD5697	Approved
0.6545	Remote Similarity	NPD5695	Phase 3
0.6535	Remote Similarity	NPD8074	Phase 3
0.6514	Remote Similarity	NPD5778	Approved
0.6514	Remote Similarity	NPD5779	Approved
0.6509	Remote Similarity	NPD7524	Approved
0.6505	Remote Similarity	NPD6435	Approved
0.6496	Remote Similarity	NPD6899	Approved
0.6496	Remote Similarity	NPD6881	Approved
0.6496	Remote Similarity	NPD7320	Approved
0.6475	Remote Similarity	NPD6009	Approved
0.6471	Remote Similarity	NPD6650	Approved
0.6471	Remote Similarity	NPD6649	Approved
0.646	Remote Similarity	NPD6648	Approved
0.6441	Remote Similarity	NPD6014	Approved
0.6441	Remote Similarity	NPD6013	Approved
0.6441	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD7604	Phase 2
0.6422	Remote Similarity	NPD6411	Approved
0.6417	Remote Similarity	NPD6882	Approved
0.6408	Remote Similarity	NPD5369	Approved
0.6404	Remote Similarity	NPD4159	Approved
0.64	Remote Similarity	NPD5983	Phase 2
0.6389	Remote Similarity	NPD1695	Approved
0.6387	Remote Similarity	NPD7102	Approved
0.6387	Remote Similarity	NPD6883	Approved
0.6387	Remote Similarity	NPD7290	Approved
0.6381	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD6399	Phase 3
0.6356	Remote Similarity	NPD6011	Approved
0.6346	Remote Similarity	NPD4269	Approved
0.6346	Remote Similarity	NPD4270	Approved
0.6333	Remote Similarity	NPD6869	Approved
0.6333	Remote Similarity	NPD8130	Phase 1
0.6333	Remote Similarity	NPD6617	Approved
0.6333	Remote Similarity	NPD6847	Approved
0.6311	Remote Similarity	NPD5368	Approved
0.6306	Remote Similarity	NPD5282	Discontinued
0.6303	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD8328	Phase 3
0.6286	Remote Similarity	NPD6695	Phase 3
0.6286	Remote Similarity	NPD5362	Discontinued
0.6286	Remote Similarity	NPD7154	Phase 3
0.6283	Remote Similarity	NPD4755	Approved
0.6273	Remote Similarity	NPD5693	Phase 1
0.6262	Remote Similarity	NPD7146	Approved
0.6262	Remote Similarity	NPD5330	Approved
0.6262	Remote Similarity	NPD5786	Approved
0.6262	Remote Similarity	NPD7521	Approved
0.6262	Remote Similarity	NPD6409	Approved
0.6262	Remote Similarity	NPD7334	Approved
0.6262	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6101	Approved
0.6239	Remote Similarity	NPD4753	Phase 2
0.6231	Remote Similarity	NPD6033	Approved
0.6226	Remote Similarity	NPD3133	Approved
0.6226	Remote Similarity	NPD3665	Phase 1
0.6226	Remote Similarity	NPD3666	Approved
0.6226	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4202	Approved
0.6212	Remote Similarity	NPD7260	Phase 2
0.621	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5211	Phase 2
0.6204	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD8273	Phase 1
0.6202	Remote Similarity	NPD6336	Discontinued
0.6198	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5209	Approved
0.6174	Remote Similarity	NPD5285	Approved
0.6174	Remote Similarity	NPD5286	Approved
0.6174	Remote Similarity	NPD4700	Approved
0.6174	Remote Similarity	NPD4696	Approved
0.6168	Remote Similarity	NPD5363	Approved
0.6168	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD4252	Approved
0.6147	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6903	Approved
0.6142	Remote Similarity	NPD6921	Approved
0.6136	Remote Similarity	NPD5956	Approved
0.6132	Remote Similarity	NPD5331	Approved
0.6132	Remote Similarity	NPD5332	Approved
0.6129	Remote Similarity	NPD6274	Approved
0.6126	Remote Similarity	NPD5284	Approved
0.6126	Remote Similarity	NPD5281	Approved
0.6117	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4522	Approved
0.6106	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5141	Approved
0.6095	Remote Similarity	NPD4790	Discontinued
0.6078	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD4633	Approved
0.6068	Remote Similarity	NPD5224	Approved
0.6068	Remote Similarity	NPD5225	Approved
0.6068	Remote Similarity	NPD5226	Approved
0.6055	Remote Similarity	NPD7750	Discontinued
0.6053	Remote Similarity	NPD7839	Suspended
0.6053	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.605	Remote Similarity	NPD4768	Approved
0.605	Remote Similarity	NPD4767	Approved
0.6047	Remote Similarity	NPD7830	Approved
0.6047	Remote Similarity	NPD7829	Approved
0.6047	Remote Similarity	NPD6067	Discontinued
0.6042	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD3667	Approved
0.6038	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5174	Approved
0.6017	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD7525	Registered
0.6	Remote Similarity	NPD6930	Phase 2
0.6	Remote Similarity	NPD6685	Approved
0.6	Remote Similarity	NPD6931	Approved
0.5984	Remote Similarity	NPD7101	Approved
0.5984	Remote Similarity	NPD7100	Approved
0.5983	Remote Similarity	NPD1700	Approved
0.5983	Remote Similarity	NPD5223	Approved
0.5965	Remote Similarity	NPD5210	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