NPASS Compound

Structure

NPC52585 OpenBabel07101719522D 33 38 0 0 1 0 0 0 0 0999 V2000 2.4271 2.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8966 1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3559 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3559 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9540 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7045 2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 2.1756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3559 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2219 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4899 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8200 -2.3090 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 -1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8200 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9540 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4899 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0880 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0880 -2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6861 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6861 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9540 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 1.9945 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 14 2 0 0 0 0 2 15 1 0 0 0 0 4 25 1 0 0 0 0 5 10 1 0 0 0 0 5 14 1 0 0 0 0 6 9 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 24 1 0 0 0 0 9 26 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 32 1 0 0 0 0 15 21 1 0 0 0 0 15 27 1 6 0 0 0 16 6 1 6 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 25 1 1 0 0 0 18 24 1 1 0 0 0 19 22 1 0 0 0 0 19 28 1 1 0 0 0 20 11 1 1 0 0 0 20 21 1 0 0 0 0 20 33 1 0 0 0 0 21 24 1 1 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 25 1 1 0 0 0 23 30 1 0 0 0 0 24 3 1 1 0 0 0 25 26 1 1 0 0 0 26 31 1 1 0 0 0 27 10 1 1 0 0 0 27 32 1 0 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.3
Volume:	474.314
LogP:	2.475
LogD:	2.803
LogS:	-3.86
# Rotatable Bonds:	0
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	5.889
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.015
MDCK Permeability:	6.951342129468685e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.42
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.527
30% Bioavailability (F30%):	0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.389
Plasma Protein Binding (PPB):	40.56934356689453%
Volume Distribution (VD):	0.742
Pgp-substrate:	53.270965576171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.913
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.715
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.378
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	9.74
Half-life (T1/2):	0.367

ADMET: Toxicity

hERG Blockers:	0.651
Human Hepatotoxicity (H-HT):	0.496
Drug-inuced Liver Injury (DILI):	0.214
AMES Toxicity:	0.18
Rat Oral Acute Toxicity:	0.823
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.826
Carcinogencity:	0.914
Eye Corrosion:	0.028
Eye Irritation:	0.029
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC52585

Natural Product ID:	NPC52585
*Common Name:**	Tupichigenin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QJHBFAPCBZSCME-UASLHZFFSA-N
Standard InCHI:	InChI=1S/C27H42O6/c1-14-5-10-27(32-13-14)15(2)21-20(33-27)11-18-16-6-9-26(31)12-19(28)22(29)23(30)25(26,4)17(16)7-8-24(18,21)3/h15-23,28-31H,1,5-13H2,2-4H3/t15-,16+,17-,18-,19+,20-,21-,22+,23+,24-,25-,26-,27+/m0/s1
SMILES:	C=C1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC[C@@]6(C[C@H]([C@H]([C@H]([C@]6(C)[C@H]5CC[C@]34C)O)O)O)O)O2)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463609
PubChem CID:	10552033
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO31092	Tupistra chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608845]
NPO31092	Tupistra chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
NPT4162	Cell Line	NUGC	Homo sapiens	Inhibition	=	42.0	%	PMID[570415]

☑ 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 NPC52585 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	286
0.1-0.2	2482
0.2-0.3	7301
0.3-0.4	13916
0.4-0.5	7998
0.5-0.6	5048
0.6-0.7	3949
0.7-0.8	1489
0.8-0.85	199
0.85-0.9	20
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC228049
1.0	High Similarity	NPC68630
0.94	High Similarity	NPC473570
0.9109	High Similarity	NPC473517
0.8889	High Similarity	NPC471112
0.8835	High Similarity	NPC128133
0.8824	High Similarity	NPC54619
0.8738	High Similarity	NPC476513
0.87	High Similarity	NPC176406
0.8654	High Similarity	NPC151134
0.8627	High Similarity	NPC475521
0.8614	High Similarity	NPC177701
0.86	High Similarity	NPC471247
0.8571	High Similarity	NPC30477
0.8571	High Similarity	NPC470867
0.8558	High Similarity	NPC49032
0.8558	High Similarity	NPC51172
0.8558	High Similarity	NPC125324
0.8557	High Similarity	NPC296620
0.8544	High Similarity	NPC474015
0.8529	High Similarity	NPC475701
0.8526	High Similarity	NPC473436
0.8515	High Similarity	NPC31346
0.8515	High Similarity	NPC474022
0.8515	High Similarity	NPC470168
0.8485	Intermediate Similarity	NPC472989
0.8447	Intermediate Similarity	NPC474464
0.8431	Intermediate Similarity	NPC31085
0.8416	Intermediate Similarity	NPC91497
0.8404	Intermediate Similarity	NPC273290
0.8404	Intermediate Similarity	NPC232044
0.84	Intermediate Similarity	NPC76486
0.84	Intermediate Similarity	NPC274793
0.84	Intermediate Similarity	NPC177818
0.8396	Intermediate Similarity	NPC191439
0.8396	Intermediate Similarity	NPC103627
0.8396	Intermediate Similarity	NPC170974
0.8384	Intermediate Similarity	NPC473348
0.8364	Intermediate Similarity	NPC83287
0.835	Intermediate Similarity	NPC471467
0.835	Intermediate Similarity	NPC213190
0.8333	Intermediate Similarity	NPC49532
0.8318	Intermediate Similarity	NPC208189
0.8318	Intermediate Similarity	NPC13190
0.8318	Intermediate Similarity	NPC65034
0.8317	Intermediate Similarity	NPC275865
0.8317	Intermediate Similarity	NPC469725
0.8316	Intermediate Similarity	NPC121981
0.8302	Intermediate Similarity	NPC475030
0.8302	Intermediate Similarity	NPC473318
0.8302	Intermediate Similarity	NPC474573
0.8302	Intermediate Similarity	NPC473328
0.8302	Intermediate Similarity	NPC28844
0.8298	Intermediate Similarity	NPC227260
0.8286	Intermediate Similarity	NPC470170
0.8286	Intermediate Similarity	NPC226642
0.8286	Intermediate Similarity	NPC470169
0.8283	Intermediate Similarity	NPC477224
0.8283	Intermediate Similarity	NPC113500
0.8283	Intermediate Similarity	NPC3538
0.8273	Intermediate Similarity	NPC27507
0.8273	Intermediate Similarity	NPC142066
0.8273	Intermediate Similarity	NPC309034
0.8273	Intermediate Similarity	NPC34390
0.8273	Intermediate Similarity	NPC87250
0.8273	Intermediate Similarity	NPC100048
0.8273	Intermediate Similarity	NPC158344
0.8273	Intermediate Similarity	NPC196429
0.8273	Intermediate Similarity	NPC77319
0.8273	Intermediate Similarity	NPC84987
0.8273	Intermediate Similarity	NPC474418
0.8273	Intermediate Similarity	NPC99728
0.8273	Intermediate Similarity	NPC50305
0.8273	Intermediate Similarity	NPC473852
0.8273	Intermediate Similarity	NPC471355
0.8273	Intermediate Similarity	NPC20979
0.8273	Intermediate Similarity	NPC471354
0.8273	Intermediate Similarity	NPC243196
0.8273	Intermediate Similarity	NPC244402
0.8273	Intermediate Similarity	NPC157376
0.8273	Intermediate Similarity	NPC471351
0.8273	Intermediate Similarity	NPC476690
0.8273	Intermediate Similarity	NPC152615
0.8273	Intermediate Similarity	NPC471353
0.8269	Intermediate Similarity	NPC471111
0.8269	Intermediate Similarity	NPC475365
0.8265	Intermediate Similarity	NPC219516
0.8265	Intermediate Similarity	NPC130840
0.8257	Intermediate Similarity	NPC31354
0.8257	Intermediate Similarity	NPC471633
0.8257	Intermediate Similarity	NPC84949
0.8257	Intermediate Similarity	NPC69576
0.8252	Intermediate Similarity	NPC22634
0.8241	Intermediate Similarity	NPC475354
0.8241	Intermediate Similarity	NPC473567
0.8241	Intermediate Similarity	NPC112274
0.8241	Intermediate Similarity	NPC231797
0.8241	Intermediate Similarity	NPC216595
0.8224	Intermediate Similarity	NPC65155
0.8218	Intermediate Similarity	NPC476893
0.8214	Intermediate Similarity	NPC474466
0.8214	Intermediate Similarity	NPC475136
0.8208	Intermediate Similarity	NPC475634
0.8198	Intermediate Similarity	NPC10366
0.8191	Intermediate Similarity	NPC211135
0.8191	Intermediate Similarity	NPC216420
0.8191	Intermediate Similarity	NPC85095
0.819	Intermediate Similarity	NPC26798
0.8182	Intermediate Similarity	NPC167644
0.8182	Intermediate Similarity	NPC199428
0.8182	Intermediate Similarity	NPC5311
0.8182	Intermediate Similarity	NPC310341
0.8182	Intermediate Similarity	NPC193382
0.8182	Intermediate Similarity	NPC99620
0.8182	Intermediate Similarity	NPC311246
0.8173	Intermediate Similarity	NPC471886
0.8173	Intermediate Similarity	NPC471888
0.8173	Intermediate Similarity	NPC471885
0.8173	Intermediate Similarity	NPC471887
0.8165	Intermediate Similarity	NPC51154
0.8155	Intermediate Similarity	NPC309425
0.8155	Intermediate Similarity	NPC160734
0.8155	Intermediate Similarity	NPC47566
0.8155	Intermediate Similarity	NPC144486
0.8155	Intermediate Similarity	NPC88000
0.8155	Intermediate Similarity	NPC129372
0.8155	Intermediate Similarity	NPC4831
0.8155	Intermediate Similarity	NPC472023
0.8148	Intermediate Similarity	NPC470311
0.8144	Intermediate Similarity	NPC128475
0.8137	Intermediate Similarity	NPC216260
0.8137	Intermediate Similarity	NPC5358
0.8137	Intermediate Similarity	NPC234287
0.8137	Intermediate Similarity	NPC476895
0.8137	Intermediate Similarity	NPC280825
0.8131	Intermediate Similarity	NPC157530
0.8131	Intermediate Similarity	NPC14630
0.8131	Intermediate Similarity	NPC472901
0.8131	Intermediate Similarity	NPC250089
0.8125	Intermediate Similarity	NPC471240
0.8125	Intermediate Similarity	NPC329905
0.8119	Intermediate Similarity	NPC292718
0.8119	Intermediate Similarity	NPC111834
0.8119	Intermediate Similarity	NPC306797
0.8119	Intermediate Similarity	NPC169270
0.8113	Intermediate Similarity	NPC473469
0.8113	Intermediate Similarity	NPC470166
0.8108	Intermediate Similarity	NPC93883
0.8108	Intermediate Similarity	NPC290693
0.8105	Intermediate Similarity	NPC255882
0.81	Intermediate Similarity	NPC3359
0.8095	Intermediate Similarity	NPC273879
0.8095	Intermediate Similarity	NPC476361
0.8095	Intermediate Similarity	NPC165033
0.8095	Intermediate Similarity	NPC312774
0.8095	Intermediate Similarity	NPC476360
0.8091	Intermediate Similarity	NPC11548
0.8085	Intermediate Similarity	NPC296734
0.8081	Intermediate Similarity	NPC5632
0.8081	Intermediate Similarity	NPC48463
0.8081	Intermediate Similarity	NPC293609
0.8081	Intermediate Similarity	NPC149966
0.8077	Intermediate Similarity	NPC300399
0.8077	Intermediate Similarity	NPC37207
0.8077	Intermediate Similarity	NPC136816
0.8077	Intermediate Similarity	NPC471482
0.807	Intermediate Similarity	NPC264336
0.8061	Intermediate Similarity	NPC228059
0.8058	Intermediate Similarity	NPC7341
0.8058	Intermediate Similarity	NPC473200
0.8058	Intermediate Similarity	NPC317019
0.8053	Intermediate Similarity	NPC475556
0.8053	Intermediate Similarity	NPC475629
0.8041	Intermediate Similarity	NPC210658
0.8041	Intermediate Similarity	NPC161928
0.8039	Intermediate Similarity	NPC477223
0.8039	Intermediate Similarity	NPC477222
0.8039	Intermediate Similarity	NPC316604
0.8037	Intermediate Similarity	NPC476538
0.8037	Intermediate Similarity	NPC476541
0.8037	Intermediate Similarity	NPC476540
0.8037	Intermediate Similarity	NPC220427
0.8037	Intermediate Similarity	NPC476539
0.802	Intermediate Similarity	NPC241047
0.8019	Intermediate Similarity	NPC472898
0.8019	Intermediate Similarity	NPC472900
0.8019	Intermediate Similarity	NPC472899
0.8018	Intermediate Similarity	NPC477029
0.8018	Intermediate Similarity	NPC477030
0.8	Intermediate Similarity	NPC120123
0.8	Intermediate Similarity	NPC189852
0.8	Intermediate Similarity	NPC472252
0.8	Intermediate Similarity	NPC242419
0.8	Intermediate Similarity	NPC155010
0.8	Intermediate Similarity	NPC31907
0.8	Intermediate Similarity	NPC245280
0.8	Intermediate Similarity	NPC144068
0.8	Intermediate Similarity	NPC286969
0.8	Intermediate Similarity	NPC232023
0.8	Intermediate Similarity	NPC476693

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 NPC52585 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	2697
0.2-0.3	4156
0.3-0.4	1316
0.4-0.5	369
0.5-0.6	234
0.6-0.7	93
0.7-0.8	15
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8455	Intermediate Similarity	NPD7516	Approved
0.8364	Intermediate Similarity	NPD7327	Approved
0.8364	Intermediate Similarity	NPD7328	Approved
0.7982	Intermediate Similarity	NPD8378	Approved
0.7982	Intermediate Similarity	NPD8335	Approved
0.7982	Intermediate Similarity	NPD8380	Approved
0.7982	Intermediate Similarity	NPD8379	Approved
0.7982	Intermediate Similarity	NPD8296	Approved
0.7895	Intermediate Similarity	NPD8294	Approved
0.7895	Intermediate Similarity	NPD8377	Approved
0.7872	Intermediate Similarity	NPD6928	Phase 2
0.7826	Intermediate Similarity	NPD8033	Approved
0.7679	Intermediate Similarity	NPD8133	Approved
0.7647	Intermediate Similarity	NPD8171	Discontinued
0.7563	Intermediate Similarity	NPD7507	Approved
0.7521	Intermediate Similarity	NPD7319	Approved
0.7373	Intermediate Similarity	NPD7503	Approved
0.7143	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.713	Intermediate Similarity	NPD7638	Approved
0.7064	Intermediate Similarity	NPD7639	Approved
0.7064	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD6054	Approved
0.699	Remote Similarity	NPD7524	Approved
0.6964	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6370	Approved
0.688	Remote Similarity	NPD7736	Approved
0.6863	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7991	Discontinued
0.6809	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6016	Approved
0.6803	Remote Similarity	NPD6015	Approved
0.6774	Remote Similarity	NPD7492	Approved
0.6765	Remote Similarity	NPD6695	Phase 3
0.6748	Remote Similarity	NPD5988	Approved
0.6729	Remote Similarity	NPD8034	Phase 2
0.6729	Remote Similarity	NPD8035	Phase 2
0.6724	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6616	Approved
0.6696	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD7078	Approved
0.6638	Remote Similarity	NPD6686	Approved
0.6637	Remote Similarity	NPD7632	Discontinued
0.6635	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6882	Approved
0.6535	Remote Similarity	NPD7645	Phase 2
0.6522	Remote Similarity	NPD7625	Phase 1
0.6509	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7750	Discontinued
0.6496	Remote Similarity	NPD7320	Approved
0.6484	Remote Similarity	NPD6033	Approved
0.6475	Remote Similarity	NPD6009	Approved
0.6471	Remote Similarity	NPD6930	Phase 2
0.6471	Remote Similarity	NPD6931	Approved
0.6466	Remote Similarity	NPD7128	Approved
0.6466	Remote Similarity	NPD5739	Approved
0.6466	Remote Similarity	NPD6675	Approved
0.6466	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD6067	Discontinued
0.6412	Remote Similarity	NPD8449	Approved
0.6404	Remote Similarity	NPD5344	Discontinued
0.64	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6051	Approved
0.6387	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6929	Approved
0.6364	Remote Similarity	NPD8450	Suspended
0.6364	Remote Similarity	NPD4632	Approved
0.6356	Remote Similarity	NPD6899	Approved
0.6356	Remote Similarity	NPD6881	Approved
0.6341	Remote Similarity	NPD7115	Discovery
0.6325	Remote Similarity	NPD6008	Approved
0.632	Remote Similarity	NPD6319	Approved
0.6303	Remote Similarity	NPD6373	Approved
0.6303	Remote Similarity	NPD6372	Approved
0.63	Remote Similarity	NPD6942	Approved
0.63	Remote Similarity	NPD7339	Approved
0.6286	Remote Similarity	NPD4788	Approved
0.6283	Remote Similarity	NPD4755	Approved
0.6281	Remote Similarity	NPD8297	Approved
0.6273	Remote Similarity	NPD7087	Discontinued
0.6271	Remote Similarity	NPD5697	Approved
0.6271	Remote Similarity	NPD5701	Approved
0.627	Remote Similarity	NPD6921	Approved
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD4634	Approved
0.6238	Remote Similarity	NPD6933	Approved
0.6228	Remote Similarity	NPD4225	Approved
0.6224	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4787	Phase 1
0.6216	Remote Similarity	NPD4202	Approved
0.621	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5211	Phase 2
0.6198	Remote Similarity	NPD6649	Approved
0.6198	Remote Similarity	NPD6869	Approved
0.6198	Remote Similarity	NPD6650	Approved
0.6198	Remote Similarity	NPD6617	Approved
0.6198	Remote Similarity	NPD8130	Phase 1
0.6198	Remote Similarity	NPD6847	Approved
0.6182	Remote Similarity	NPD3168	Discontinued
0.6176	Remote Similarity	NPD5776	Phase 2
0.6176	Remote Similarity	NPD6932	Approved
0.6176	Remote Similarity	NPD6925	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
0.6172	Remote Similarity	NPD8328	Phase 3
0.6168	Remote Similarity	NPD6893	Approved
0.6167	Remote Similarity	NPD6014	Approved
0.6167	Remote Similarity	NPD6012	Approved
0.6167	Remote Similarity	NPD6013	Approved
0.6162	Remote Similarity	NPD4243	Approved
0.6154	Remote Similarity	NPD4748	Discontinued
0.6154	Remote Similarity	NPD7514	Phase 3
0.6148	Remote Similarity	NPD6053	Discontinued
0.614	Remote Similarity	NPD6083	Phase 2
0.614	Remote Similarity	NPD6084	Phase 2
0.6134	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6115	Approved
0.6117	Remote Similarity	NPD6114	Approved
0.6117	Remote Similarity	NPD6697	Approved
0.6117	Remote Similarity	NPD6118	Approved
0.6117	Remote Similarity	NPD7145	Approved
0.6105	Remote Similarity	NPD371	Approved
0.6102	Remote Similarity	NPD5141	Approved
0.6083	Remote Similarity	NPD6011	Approved
0.6071	Remote Similarity	NPD6399	Phase 3
0.6068	Remote Similarity	NPD4633	Approved
0.6068	Remote Similarity	NPD5224	Approved
0.6068	Remote Similarity	NPD5225	Approved
0.6068	Remote Similarity	NPD5226	Approved
0.6066	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6683	Phase 2
0.6047	Remote Similarity	NPD7604	Phase 2
0.604	Remote Similarity	NPD6926	Approved
0.604	Remote Similarity	NPD4784	Approved
0.604	Remote Similarity	NPD4785	Approved
0.604	Remote Similarity	NPD1811	Approved
0.604	Remote Similarity	NPD1810	Approved
0.604	Remote Similarity	NPD6924	Approved
0.6034	Remote Similarity	NPD6648	Approved
0.6019	Remote Similarity	NPD6116	Phase 1
0.6017	Remote Similarity	NPD5174	Approved
0.6017	Remote Similarity	NPD5175	Approved
0.6016	Remote Similarity	NPD8517	Approved
0.6016	Remote Similarity	NPD8515	Approved
0.6016	Remote Similarity	NPD8513	Phase 3
0.6016	Remote Similarity	NPD8516	Approved
0.6016	Remote Similarity	NPD5983	Phase 2
0.6015	Remote Similarity	NPD5956	Approved
0.6	Remote Similarity	NPD7332	Phase 2
0.5983	Remote Similarity	NPD1700	Approved
0.5983	Remote Similarity	NPD5223	Approved
0.5982	Remote Similarity	NPD7637	Suspended
0.5965	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD6336	Discontinued
0.5946	Remote Similarity	NPD4753	Phase 2
0.5946	Remote Similarity	NPD5328	Approved
0.5943	Remote Similarity	NPD6898	Phase 1
0.5943	Remote Similarity	NPD6902	Approved
0.5935	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4786	Approved
0.5922	Remote Similarity	NPD6117	Approved
0.5917	Remote Similarity	NPD4767	Approved
0.5917	Remote Similarity	NPD4768	Approved
0.5882	Remote Similarity	NPD4754	Approved
0.5877	Remote Similarity	NPD7748	Approved
0.5873	Remote Similarity	NPD6274	Approved
0.5873	Remote Similarity	NPD6940	Discontinued
0.5862	Remote Similarity	NPD7902	Approved
0.5859	Remote Similarity	NPD7100	Approved
0.5859	Remote Similarity	NPD7101	Approved
0.5856	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7509	Discontinued
0.5841	Remote Similarity	NPD6079	Approved
0.5841	Remote Similarity	NPD7515	Phase 2
0.5826	Remote Similarity	NPD5695	Phase 3
0.5825	Remote Similarity	NPD4190	Phase 3
0.5825	Remote Similarity	NPD5275	Approved
0.582	Remote Similarity	NPD8174	Phase 2
0.582	Remote Similarity	NPD5128	Approved
0.582	Remote Similarity	NPD4730	Approved
0.582	Remote Similarity	NPD4729	Approved
0.5818	Remote Similarity	NPD3618	Phase 1
0.5814	Remote Similarity	NPD7741	Discontinued
0.5812	Remote Similarity	NPD5696	Approved
0.5789	Remote Similarity	NPD1145	Discontinued
0.5785	Remote Similarity	NPD5357	Phase 1
0.5785	Remote Similarity	NPD6640	Phase 3
0.5781	Remote Similarity	NPD6335	Approved
0.578	Remote Similarity	NPD3665	Phase 1
0.578	Remote Similarity	NPD3666	Approved
0.578	Remote Similarity	NPD3133	Approved
0.5769	Remote Similarity	NPD6908	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