NPASS Compound

Structure

CID79449 OpenBabel06191715412D 31 34 0 0 1 0 0 0 0 0999 V2000 4.6300 1.1633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9838 1.1755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2063 -3.1288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2173 -3.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1057 -1.7619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8069 0.6881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3269 1.1816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3269 -0.7438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4932 -1.2250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0359 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1606 0.7003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1023 -2.7771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5418 -2.3292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1606 -0.2624 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4932 0.7003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8069 -0.2624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6157 0.2188 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1979 -0.6486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1981 1.0863 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2594 -0.8626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4932 -0.2624 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3977 0.2711 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8550 -3.3773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6101 -2.5713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6300 -0.7377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5367 0.2187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2458 -1.8252 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 -1.7980 -1.4013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9838 -0.7377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2596 1.3004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 20 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 8 21 1 0 0 0 0 9 27 1 0 0 0 0 10 22 1 0 0 0 0 10 28 1 0 0 0 0 11 14 1 0 0 0 0 12 23 2 0 0 0 0 12 27 1 0 0 0 0 13 24 2 0 0 0 0 13 29 1 0 0 0 0 14 30 1 1 0 0 0 15 21 1 6 0 0 0 15 31 1 0 0 0 0 16 25 2 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 1 0 0 0 18 20 1 6 0 0 0 18 29 1 0 0 0 0 19 22 1 6 0 0 0 19 31 1 0 0 0 0 20 21 1 1 0 0 0 21 9 1 1 0 0 0 22 20 1 1 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.19
Volume:	423.409
LogP:	1.862
LogD:	1.263
LogS:	-4.151
# Rotatable Bonds:	8
TPSA:	120.89
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	6.063
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.324
MDCK Permeability:	6.332520570140332e-05
Pgp-inhibitor:	0.442
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.107
20% Bioavailability (F20%):	0.572
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.426
Plasma Protein Binding (PPB):	32.45965576171875%
Volume Distribution (VD):	1.125
Pgp-substrate:	42.703880310058594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.399
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.573
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	2.828
Half-life (T1/2):	0.756

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.503
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.937
Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.298
Skin Sensitization:	0.432
Carcinogencity:	0.09
Eye Corrosion:	0.004
Eye Irritation:	0.026
Respiratory Toxicity:	0.191

Download Data

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

Natural Product: NPC79449

Natural Product ID:	NPC79449
*Common Name:**	ZSGWJLBSFZRJAT-MLXHEQMXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZSGWJLBSFZRJAT-MLXHEQMXSA-N
Standard InCHI:	InChI=1S/C22H30O9/c1-6-16(25)30-14-8-21(9-27-12(3)23)15(7-11(14)2)31-19-17(26)18(29-13(4)24)20(21,5)22(19)10-28-22/h7,14-15,17-19,26H,6,8-10H2,1-5H3/t14-,15+,17+,18+,19+,20+,21+,22-/m0/s1
SMILES:	CCC(=O)O[C@H]1C[C@@]2(COC(=O)C)[C@@H](C=C1C)O[C@@H]1[C@@H]([C@H]([C@@]2(C)[C@@]21CO2)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL422681
PubChem CID:	183169
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
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800633]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8289061]
NPO10844	Lactarius pergamenus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4524	Bosistoa pentacocca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10844	Lactarius pergamenus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11220	Fusarium sporotrichioides	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	LC50	=	0.0016	ug.mL-1	PMID[515734]

☑ 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 NPC79449 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	184
0.1-0.2	1248
0.2-0.3	4862
0.3-0.4	13123
0.4-0.5	9603
0.5-0.6	7197
0.6-0.7	5590
0.7-0.8	816
0.8-0.85	18
0.85-0.9	21
0.9-0.95	18
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474957
0.989	High Similarity	NPC476057
0.989	High Similarity	NPC347923
0.9785	High Similarity	NPC26557
0.9783	High Similarity	NPC274458
0.9681	High Similarity	NPC475956
0.9681	High Similarity	NPC200672
0.9681	High Similarity	NPC214714
0.9681	High Similarity	NPC252242
0.9681	High Similarity	NPC475986
0.9674	High Similarity	NPC182811
0.967	High Similarity	NPC240838
0.9579	High Similarity	NPC260809
0.9579	High Similarity	NPC232515
0.9579	High Similarity	NPC474783
0.9263	High Similarity	NPC79631
0.9022	High Similarity	NPC197107
0.899	High Similarity	NPC29389
0.899	High Similarity	NPC93026
0.899	High Similarity	NPC469960
0.899	High Similarity	NPC265502
0.89	High Similarity	NPC472263
0.89	High Similarity	NPC469959
0.89	High Similarity	NPC108682
0.89	High Similarity	NPC469957
0.8824	High Similarity	NPC50223
0.8667	High Similarity	NPC265290
0.8667	High Similarity	NPC305044
0.8654	High Similarity	NPC313921
0.8654	High Similarity	NPC98038
0.8641	High Similarity	NPC41551
0.8571	High Similarity	NPC101400
0.8571	High Similarity	NPC101965
0.8485	Intermediate Similarity	NPC13743
0.8485	Intermediate Similarity	NPC98813
0.8396	Intermediate Similarity	NPC287075
0.8384	Intermediate Similarity	NPC65700
0.8257	Intermediate Similarity	NPC474286
0.8257	Intermediate Similarity	NPC475130
0.8235	Intermediate Similarity	NPC123505
0.8155	Intermediate Similarity	NPC169843
0.8077	Intermediate Similarity	NPC470980
0.8077	Intermediate Similarity	NPC475290
0.8037	Intermediate Similarity	NPC71680
0.8019	Intermediate Similarity	NPC77089
0.8	Intermediate Similarity	NPC477668
0.7981	Intermediate Similarity	NPC473577
0.7981	Intermediate Similarity	NPC475585
0.7981	Intermediate Similarity	NPC474550
0.798	Intermediate Similarity	NPC281775
0.7963	Intermediate Similarity	NPC241477
0.7963	Intermediate Similarity	NPC126691
0.7961	Intermediate Similarity	NPC470972
0.7944	Intermediate Similarity	NPC15551
0.7885	Intermediate Similarity	NPC473523
0.7885	Intermediate Similarity	NPC474124
0.7872	Intermediate Similarity	NPC231601
0.7864	Intermediate Similarity	NPC475617
0.7843	Intermediate Similarity	NPC222303
0.7822	Intermediate Similarity	NPC113433
0.7822	Intermediate Similarity	NPC57664
0.7818	Intermediate Similarity	NPC106446
0.7818	Intermediate Similarity	NPC216665
0.7812	Intermediate Similarity	NPC137253
0.781	Intermediate Similarity	NPC121518
0.781	Intermediate Similarity	NPC181104
0.781	Intermediate Similarity	NPC103298
0.781	Intermediate Similarity	NPC201144
0.781	Intermediate Similarity	NPC288502
0.781	Intermediate Similarity	NPC475331
0.781	Intermediate Similarity	NPC473543
0.781	Intermediate Similarity	NPC80809
0.781	Intermediate Similarity	NPC475335
0.7788	Intermediate Similarity	NPC475344
0.7788	Intermediate Similarity	NPC472552
0.7788	Intermediate Similarity	NPC476471
0.7767	Intermediate Similarity	NPC230546
0.7755	Intermediate Similarity	NPC299527
0.7745	Intermediate Similarity	NPC210337
0.7745	Intermediate Similarity	NPC205143
0.7736	Intermediate Similarity	NPC60315
0.7714	Intermediate Similarity	NPC475623
0.7714	Intermediate Similarity	NPC475334
0.7714	Intermediate Similarity	NPC473694
0.7714	Intermediate Similarity	NPC472821
0.7706	Intermediate Similarity	NPC474750
0.7699	Intermediate Similarity	NPC278681
0.7692	Intermediate Similarity	NPC11974
0.7692	Intermediate Similarity	NPC472554
0.7692	Intermediate Similarity	NPC280991
0.7684	Intermediate Similarity	NPC477667
0.7679	Intermediate Similarity	NPC290693
0.7679	Intermediate Similarity	NPC203862
0.767	Intermediate Similarity	NPC212465
0.767	Intermediate Similarity	NPC177232
0.7664	Intermediate Similarity	NPC475781
0.7658	Intermediate Similarity	NPC178289
0.7658	Intermediate Similarity	NPC43213
0.7652	Intermediate Similarity	NPC115349
0.7647	Intermediate Similarity	NPC88009
0.7642	Intermediate Similarity	NPC472822
0.7642	Intermediate Similarity	NPC152966
0.7632	Intermediate Similarity	NPC112936
0.7632	Intermediate Similarity	NPC79579
0.7624	Intermediate Similarity	NPC472467
0.7619	Intermediate Similarity	NPC109195
0.7619	Intermediate Similarity	NPC475038
0.7615	Intermediate Similarity	NPC472215
0.7615	Intermediate Similarity	NPC472214
0.7611	Intermediate Similarity	NPC16701
0.7596	Intermediate Similarity	NPC473510
0.7596	Intermediate Similarity	NPC130792
0.7596	Intermediate Similarity	NPC79303
0.7593	Intermediate Similarity	NPC88701
0.7589	Intermediate Similarity	NPC310341
0.7589	Intermediate Similarity	NPC99620
0.7589	Intermediate Similarity	NPC199428
0.7589	Intermediate Similarity	NPC5311
0.7589	Intermediate Similarity	NPC193382
0.7573	Intermediate Similarity	NPC155319
0.7573	Intermediate Similarity	NPC309503
0.7573	Intermediate Similarity	NPC91197
0.7573	Intermediate Similarity	NPC473244
0.7573	Intermediate Similarity	NPC475033
0.7573	Intermediate Similarity	NPC96597
0.7573	Intermediate Similarity	NPC475032
0.7573	Intermediate Similarity	NPC125551
0.7573	Intermediate Similarity	NPC239547
0.757	Intermediate Similarity	NPC85670
0.757	Intermediate Similarity	NPC119855
0.757	Intermediate Similarity	NPC220217
0.757	Intermediate Similarity	NPC186668
0.7549	Intermediate Similarity	NPC220221
0.7547	Intermediate Similarity	NPC474775
0.7545	Intermediate Similarity	NPC470076
0.7544	Intermediate Similarity	NPC44899
0.7544	Intermediate Similarity	NPC81222
0.7544	Intermediate Similarity	NPC5883
0.7544	Intermediate Similarity	NPC5292
0.7544	Intermediate Similarity	NPC291820
0.7544	Intermediate Similarity	NPC35171
0.7544	Intermediate Similarity	NPC29639
0.7544	Intermediate Similarity	NPC213761
0.7544	Intermediate Similarity	NPC304260
0.7527	Intermediate Similarity	NPC477089
0.7525	Intermediate Similarity	NPC470187
0.7524	Intermediate Similarity	NPC198992
0.7523	Intermediate Similarity	NPC472216
0.7523	Intermediate Similarity	NPC284828
0.7523	Intermediate Similarity	NPC257853
0.7523	Intermediate Similarity	NPC128133
0.7523	Intermediate Similarity	NPC187876
0.7523	Intermediate Similarity	NPC5475
0.7523	Intermediate Similarity	NPC173905
0.7522	Intermediate Similarity	NPC99728
0.7522	Intermediate Similarity	NPC50305
0.7522	Intermediate Similarity	NPC158344
0.7522	Intermediate Similarity	NPC84987
0.7522	Intermediate Similarity	NPC157380
0.7522	Intermediate Similarity	NPC93883
0.7522	Intermediate Similarity	NPC244402
0.7522	Intermediate Similarity	NPC474418
0.7522	Intermediate Similarity	NPC185287
0.7522	Intermediate Similarity	NPC309034
0.7522	Intermediate Similarity	NPC473852
0.7522	Intermediate Similarity	NPC142066
0.7522	Intermediate Similarity	NPC152615
0.7522	Intermediate Similarity	NPC471351
0.7522	Intermediate Similarity	NPC87250
0.7522	Intermediate Similarity	NPC27507
0.7522	Intermediate Similarity	NPC471353
0.7522	Intermediate Similarity	NPC471354
0.7522	Intermediate Similarity	NPC157376
0.7522	Intermediate Similarity	NPC34390
0.7522	Intermediate Similarity	NPC243196
0.7522	Intermediate Similarity	NPC196429
0.7522	Intermediate Similarity	NPC471355
0.7522	Intermediate Similarity	NPC77319
0.75	Intermediate Similarity	NPC324327
0.75	Intermediate Similarity	NPC202886
0.75	Intermediate Similarity	NPC474421
0.75	Intermediate Similarity	NPC84949
0.75	Intermediate Similarity	NPC69576
0.75	Intermediate Similarity	NPC72813
0.75	Intermediate Similarity	NPC472820
0.75	Intermediate Similarity	NPC471633
0.75	Intermediate Similarity	NPC31354
0.75	Intermediate Similarity	NPC194620
0.75	Intermediate Similarity	NPC471082
0.75	Intermediate Similarity	NPC326994
0.7478	Intermediate Similarity	NPC472004
0.7478	Intermediate Similarity	NPC107607
0.7477	Intermediate Similarity	NPC473567
0.7477	Intermediate Similarity	NPC216595
0.7477	Intermediate Similarity	NPC258532
0.7477	Intermediate Similarity	NPC200861
0.7476	Intermediate Similarity	NPC221801
0.7476	Intermediate Similarity	NPC284063
0.7476	Intermediate Similarity	NPC284194
0.7476	Intermediate Similarity	NPC211810

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 NPC79449 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1573
0.2-0.3	4078
0.3-0.4	2372
0.4-0.5	545
0.5-0.6	274
0.6-0.7	157
0.7-0.8	4
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
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.7456	Intermediate Similarity	NPD7328	Approved
0.7456	Intermediate Similarity	NPD7327	Approved
0.7414	Intermediate Similarity	NPD7503	Approved
0.7414	Intermediate Similarity	NPD8033	Approved
0.7391	Intermediate Similarity	NPD7516	Approved
0.7333	Intermediate Similarity	NPD7638	Approved
0.7328	Intermediate Similarity	NPD8377	Approved
0.7328	Intermediate Similarity	NPD8294	Approved
0.7327	Intermediate Similarity	NPD7838	Discovery
0.7265	Intermediate Similarity	NPD8379	Approved
0.7265	Intermediate Similarity	NPD8335	Approved
0.7265	Intermediate Similarity	NPD8378	Approved
0.7265	Intermediate Similarity	NPD8296	Approved
0.7265	Intermediate Similarity	NPD8380	Approved
0.7264	Intermediate Similarity	NPD7639	Approved
0.7264	Intermediate Similarity	NPD7640	Approved
0.7207	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7507	Approved
0.7117	Intermediate Similarity	NPD6686	Approved
0.7037	Intermediate Similarity	NPD5344	Discontinued
0.7034	Intermediate Similarity	NPD6319	Approved
0.7027	Intermediate Similarity	NPD6412	Phase 2
0.7018	Intermediate Similarity	NPD6053	Discontinued
0.6992	Remote Similarity	NPD7319	Approved
0.6991	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6371	Approved
0.6931	Remote Similarity	NPD4249	Approved
0.6923	Remote Similarity	NPD7115	Discovery
0.6893	Remote Similarity	NPD6051	Approved
0.6875	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4250	Approved
0.6863	Remote Similarity	NPD4251	Approved
0.6852	Remote Similarity	NPD4225	Approved
0.6837	Remote Similarity	NPD4822	Approved
0.6837	Remote Similarity	NPD4820	Approved
0.6837	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4821	Approved
0.6837	Remote Similarity	NPD4819	Approved
0.6832	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4632	Approved
0.6726	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD8297	Approved
0.6699	Remote Similarity	NPD7524	Approved
0.6697	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6638	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6402	Approved
0.6637	Remote Similarity	NPD6008	Approved
0.6637	Remote Similarity	NPD7128	Approved
0.6637	Remote Similarity	NPD5739	Approved
0.6637	Remote Similarity	NPD6675	Approved
0.6636	Remote Similarity	NPD6648	Approved
0.6633	Remote Similarity	NPD4268	Approved
0.6633	Remote Similarity	NPD4271	Approved
0.6609	Remote Similarity	NPD6372	Approved
0.6609	Remote Similarity	NPD6373	Approved
0.6606	Remote Similarity	NPD6084	Phase 2
0.6606	Remote Similarity	NPD6083	Phase 2
0.6604	Remote Similarity	NPD7637	Suspended
0.6579	Remote Similarity	NPD5697	Approved
0.6579	Remote Similarity	NPD5701	Approved
0.6577	Remote Similarity	NPD4159	Approved
0.6574	Remote Similarity	NPD5695	Phase 3
0.6569	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8517	Approved
0.6557	Remote Similarity	NPD8515	Approved
0.6557	Remote Similarity	NPD8513	Phase 3
0.6557	Remote Similarity	NPD8516	Approved
0.6535	Remote Similarity	NPD6435	Approved
0.6532	Remote Similarity	NPD7492	Approved
0.6522	Remote Similarity	NPD6899	Approved
0.6522	Remote Similarity	NPD6881	Approved
0.6522	Remote Similarity	NPD7320	Approved
0.65	Remote Similarity	NPD6009	Approved
0.6496	Remote Similarity	NPD6649	Approved
0.6496	Remote Similarity	NPD6650	Approved
0.648	Remote Similarity	NPD6616	Approved
0.6475	Remote Similarity	NPD6054	Approved
0.6475	Remote Similarity	NPD6059	Approved
0.6471	Remote Similarity	NPD6695	Phase 3
0.6466	Remote Similarity	NPD6014	Approved
0.6466	Remote Similarity	NPD6013	Approved
0.6466	Remote Similarity	NPD6012	Approved
0.6452	Remote Similarity	NPD7604	Phase 2
0.6449	Remote Similarity	NPD7983	Approved
0.6441	Remote Similarity	NPD6882	Approved
0.6429	Remote Similarity	NPD7078	Approved
0.6429	Remote Similarity	NPD8293	Discontinued
0.6423	Remote Similarity	NPD5983	Phase 2
0.6423	Remote Similarity	NPD6015	Approved
0.6423	Remote Similarity	NPD6016	Approved
0.6415	Remote Similarity	NPD1695	Approved
0.641	Remote Similarity	NPD7102	Approved
0.641	Remote Similarity	NPD4634	Approved
0.641	Remote Similarity	NPD6883	Approved
0.641	Remote Similarity	NPD7290	Approved
0.6408	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5696	Approved
0.6389	Remote Similarity	NPD6399	Phase 3
0.6381	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6011	Approved
0.6379	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7736	Approved
0.6371	Remote Similarity	NPD5988	Approved
0.6371	Remote Similarity	NPD6370	Approved
0.6356	Remote Similarity	NPD6847	Approved
0.6356	Remote Similarity	NPD6869	Approved
0.6356	Remote Similarity	NPD6617	Approved
0.6356	Remote Similarity	NPD8130	Phase 1
0.6355	Remote Similarity	NPD5785	Approved
0.6337	Remote Similarity	NPD5368	Approved
0.6325	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5362	Discontinued
0.6311	Remote Similarity	NPD7154	Phase 3
0.6306	Remote Similarity	NPD4755	Approved
0.6299	Remote Similarity	NPD8074	Phase 3
0.6296	Remote Similarity	NPD5693	Phase 1
0.6286	Remote Similarity	NPD6409	Approved
0.6286	Remote Similarity	NPD7334	Approved
0.6286	Remote Similarity	NPD5330	Approved
0.6286	Remote Similarity	NPD6684	Approved
0.6286	Remote Similarity	NPD7146	Approved
0.6286	Remote Similarity	NPD7521	Approved
0.6263	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD3666	Approved
0.6239	Remote Similarity	NPD4202	Approved
0.6239	Remote Similarity	NPD5779	Approved
0.6239	Remote Similarity	NPD5778	Approved
0.6237	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7260	Phase 2
0.6228	Remote Similarity	NPD5211	Phase 2
0.6226	Remote Similarity	NPD7750	Discontinued
0.622	Remote Similarity	NPD6336	Discontinued
0.6218	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4700	Approved
0.6195	Remote Similarity	NPD5286	Approved
0.6195	Remote Similarity	NPD4696	Approved
0.6195	Remote Similarity	NPD5285	Approved
0.619	Remote Similarity	NPD1694	Approved
0.619	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6930	Phase 2
0.6176	Remote Similarity	NPD7525	Registered
0.6176	Remote Similarity	NPD6931	Approved
0.6168	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD5331	Approved
0.6154	Remote Similarity	NPD5332	Approved
0.6148	Remote Similarity	NPD6274	Approved
0.6147	Remote Similarity	NPD5281	Approved
0.6147	Remote Similarity	NPD5284	Approved
0.6147	Remote Similarity	NPD6411	Approved
0.6139	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5141	Approved
0.6117	Remote Similarity	NPD5369	Approved
0.6117	Remote Similarity	NPD4790	Discontinued
0.61	Remote Similarity	NPD6933	Approved
0.6087	Remote Similarity	NPD5225	Approved
0.6087	Remote Similarity	NPD4633	Approved
0.6087	Remote Similarity	NPD5224	Approved
0.6087	Remote Similarity	NPD5226	Approved
0.6078	Remote Similarity	NPD6929	Approved
0.6068	Remote Similarity	NPD4768	Approved
0.6068	Remote Similarity	NPD4767	Approved
0.6063	Remote Similarity	NPD8328	Phase 3
0.6063	Remote Similarity	NPD6067	Discontinued
0.6058	Remote Similarity	NPD3667	Approved
0.6058	Remote Similarity	NPD4269	Approved
0.6058	Remote Similarity	NPD4270	Approved
0.6058	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5282	Discontinued
0.6034	Remote Similarity	NPD5175	Approved
0.6034	Remote Similarity	NPD5174	Approved
0.6019	Remote Similarity	NPD7514	Phase 3
0.6017	Remote Similarity	NPD6685	Approved
0.6	Remote Similarity	NPD7087	Discontinued
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD6033	Approved
0.6	Remote Similarity	NPD5223	Approved
0.5982	Remote Similarity	NPD5210	Approved
0.5982	Remote Similarity	NPD4629	Approved
0.5982	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6098	Approved
0.5981	Remote Similarity	NPD3618	Phase 1
0.5981	Remote Similarity	NPD5786	Approved
0.5969	Remote Similarity	NPD8273	Phase 1
0.5968	Remote Similarity	NPD6317	Approved
0.5968	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD4730	Approved
0.5966	Remote Similarity	NPD4729	Approved
0.5963	Remote Similarity	NPD6673	Approved
0.5963	Remote Similarity	NPD5764	Clinical (unspecified phase)

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