NPASS Compound

Structure

CID176406 OpenBabel06191715552D 31 36 0 0 1 0 0 0 0 0999 V2000 3.5827 -0.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3104 -2.5222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8950 -2.2523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4137 -3.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1181 -1.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2783 -1.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0760 -1.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6010 -3.2053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7613 -2.7211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0714 -1.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9581 -3.2032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1192 -4.6572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7596 0.1856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0760 0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5782 -0.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5668 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1186 -2.7195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9584 -4.1720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4391 -1.7511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4397 -2.7204 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5994 -1.2669 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9209 -0.2992 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2798 -4.1735 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9209 -1.2676 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7607 -1.7518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2795 -3.2046 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5692 -0.7834 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8246 -4.6716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4140 -4.6740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0714 0.0865 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 2 0 0 0 0 2 16 1 0 0 0 0 5 6 1 0 0 0 0 5 17 2 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 25 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 30 1 0 0 0 0 16 24 1 0 0 0 0 16 27 1 1 0 0 0 17 26 1 0 0 0 0 18 28 1 1 0 0 0 19 6 1 1 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 26 1 6 0 0 0 21 25 1 6 0 0 0 22 13 1 6 0 0 0 22 24 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 6 0 0 0 23 29 1 0 0 0 0 24 25 1 6 0 0 0 25 3 1 6 0 0 0 26 4 1 6 0 0 0 27 10 1 6 0 0 0 27 30 1 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.29
Volume:	454.097
LogP:	3.892
LogD:	3.598
LogS:	-4.697
# Rotatable Bonds:	0
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	5.578
Fsp3:	0.852
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.744
MDCK Permeability:	1.3734371350437868e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.506
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.876
Plasma Protein Binding (PPB):	52.57906723022461%
Volume Distribution (VD):	1.745
Pgp-substrate:	41.97426223754883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.569
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.678
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.304
CYP3A4-inhibitor:	0.609
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	11.924
Half-life (T1/2):	0.24

ADMET: Toxicity

hERG Blockers:	0.915
Human Hepatotoxicity (H-HT):	0.583
Drug-inuced Liver Injury (DILI):	0.552
AMES Toxicity:	0.394
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.936
Carcinogencity:	0.94
Eye Corrosion:	0.057
Eye Irritation:	0.133
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC176406

Natural Product ID:	NPC176406
*Common Name:**	ALTRINCJVPIQNK-VIBADNOWSA-N
IUPAC Name:	n.a.
Synonyms:	3-epineoruscogenin
Standard InCHIKey:	ALTRINCJVPIQNK-VIBADNOWSA-N
Standard InCHI:	InChI=1S/C27H40O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,16,18-24,28-29H,1,6-14H2,2-4H3/t16-,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=C6C[C@@H](C[C@H]([C@]6(C)[C@H]5CC[C@]34C)O)O)O2)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518521
PubChem CID:	21626040
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]
NPO28394	Rohdea chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28394	Rohdea chinensis	Species	Asparagaceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	45.0	%	PMID[544294]

☑ 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 NPC176406 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	233
0.1-0.2	1718
0.2-0.3	5378
0.3-0.4	13489
0.4-0.5	9250
0.5-0.6	5697
0.6-0.7	5082
0.7-0.8	1606
0.8-0.85	190
0.85-0.9	43
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC177818
0.9375	High Similarity	NPC474022
0.93	High Similarity	NPC128133
0.9247	High Similarity	NPC235126
0.9247	High Similarity	NPC242419
0.9118	High Similarity	NPC13190
0.9029	High Similarity	NPC112274
0.9	High Similarity	NPC474015
0.899	High Similarity	NPC475701
0.8942	High Similarity	NPC51154
0.8911	High Similarity	NPC226642
0.89	High Similarity	NPC474464
0.8857	High Similarity	NPC11548
0.8824	High Similarity	NPC476538
0.8824	High Similarity	NPC476539
0.8824	High Similarity	NPC476540
0.8824	High Similarity	NPC476541
0.88	High Similarity	NPC471886
0.88	High Similarity	NPC471887
0.88	High Similarity	NPC471885
0.88	High Similarity	NPC471888
0.8774	High Similarity	NPC477030
0.8774	High Similarity	NPC477029
0.8738	High Similarity	NPC70204
0.8738	High Similarity	NPC475670
0.8738	High Similarity	NPC306131
0.8738	High Similarity	NPC477026
0.8738	High Similarity	NPC477027
0.8713	High Similarity	NPC93352
0.8713	High Similarity	NPC471111
0.87	High Similarity	NPC37207
0.87	High Similarity	NPC228049
0.87	High Similarity	NPC471482
0.87	High Similarity	NPC300399
0.87	High Similarity	NPC68630
0.87	High Similarity	NPC52585
0.8667	High Similarity	NPC42171
0.8654	High Similarity	NPC103627
0.8654	High Similarity	NPC191439
0.8654	High Similarity	NPC170974
0.8627	High Similarity	NPC181845
0.8627	High Similarity	NPC473923
0.8627	High Similarity	NPC473476
0.8614	High Similarity	NPC471450
0.8611	High Similarity	NPC475403
0.8611	High Similarity	NPC160888
0.8598	High Similarity	NPC148965
0.8586	High Similarity	NPC275865
0.8586	High Similarity	NPC309493
0.8571	High Similarity	NPC208189
0.8571	High Similarity	NPC475247
0.8571	High Similarity	NPC294129
0.8571	High Similarity	NPC65034
0.8558	High Similarity	NPC250089
0.8558	High Similarity	NPC475030
0.8558	High Similarity	NPC157530
0.8558	High Similarity	NPC28844
0.8558	High Similarity	NPC473328
0.8558	High Similarity	NPC14630
0.8558	High Similarity	NPC473318
0.8544	High Similarity	NPC230507
0.8544	High Similarity	NPC470432
0.8544	High Similarity	NPC33053
0.8544	High Similarity	NPC283829
0.8544	High Similarity	NPC161676
0.8544	High Similarity	NPC113044
0.8544	High Similarity	NPC14704
0.8544	High Similarity	NPC305423
0.8532	High Similarity	NPC473633
0.8532	High Similarity	NPC229962
0.8532	High Similarity	NPC476085
0.8532	High Similarity	NPC195560
0.8515	High Similarity	NPC471889
0.8515	High Similarity	NPC22634
0.8491	Intermediate Similarity	NPC473567
0.8491	Intermediate Similarity	NPC216595
0.8491	Intermediate Similarity	NPC231797
0.8485	Intermediate Similarity	NPC473890
0.8485	Intermediate Similarity	NPC243728
0.8476	Intermediate Similarity	NPC65155
0.8476	Intermediate Similarity	NPC141433
0.8469	Intermediate Similarity	NPC100892
0.8469	Intermediate Similarity	NPC477969
0.8469	Intermediate Similarity	NPC135224
0.8469	Intermediate Similarity	NPC477970
0.8462	Intermediate Similarity	NPC98696
0.8455	Intermediate Similarity	NPC50689
0.8455	Intermediate Similarity	NPC233391
0.8455	Intermediate Similarity	NPC207243
0.8455	Intermediate Similarity	NPC198325
0.8447	Intermediate Similarity	NPC26798
0.8447	Intermediate Similarity	NPC242748
0.8416	Intermediate Similarity	NPC285231
0.8416	Intermediate Similarity	NPC471112
0.8416	Intermediate Similarity	NPC21568
0.8416	Intermediate Similarity	NPC470434
0.84	Intermediate Similarity	NPC158088
0.84	Intermediate Similarity	NPC5358
0.84	Intermediate Similarity	NPC216260
0.8396	Intermediate Similarity	NPC197231
0.8384	Intermediate Similarity	NPC207617
0.8381	Intermediate Similarity	NPC470433
0.8381	Intermediate Similarity	NPC475333
0.8381	Intermediate Similarity	NPC95051
0.8381	Intermediate Similarity	NPC249265
0.8381	Intermediate Similarity	NPC22779
0.8381	Intermediate Similarity	NPC171073
0.8381	Intermediate Similarity	NPC218571
0.8381	Intermediate Similarity	NPC40440
0.8381	Intermediate Similarity	NPC224098
0.8381	Intermediate Similarity	NPC248746
0.8381	Intermediate Similarity	NPC150372
0.8381	Intermediate Similarity	NPC73243
0.8381	Intermediate Similarity	NPC232054
0.8381	Intermediate Similarity	NPC208383
0.8381	Intermediate Similarity	NPC42482
0.8381	Intermediate Similarity	NPC194207
0.8381	Intermediate Similarity	NPC475550
0.8381	Intermediate Similarity	NPC477809
0.8381	Intermediate Similarity	NPC244086
0.8381	Intermediate Similarity	NPC300557
0.8381	Intermediate Similarity	NPC84956
0.8381	Intermediate Similarity	NPC102016
0.8381	Intermediate Similarity	NPC46190
0.8381	Intermediate Similarity	NPC309278
0.8381	Intermediate Similarity	NPC6806
0.8367	Intermediate Similarity	NPC189513
0.8367	Intermediate Similarity	NPC144202
0.8365	Intermediate Similarity	NPC473469
0.8365	Intermediate Similarity	NPC475781
0.835	Intermediate Similarity	NPC75608
0.835	Intermediate Similarity	NPC475365
0.8349	Intermediate Similarity	NPC203862
0.8318	Intermediate Similarity	NPC19888
0.8318	Intermediate Similarity	NPC477050
0.8317	Intermediate Similarity	NPC471242
0.8317	Intermediate Similarity	NPC282669
0.8317	Intermediate Similarity	NPC469942
0.8317	Intermediate Similarity	NPC324598
0.8304	Intermediate Similarity	NPC43842
0.8302	Intermediate Similarity	NPC247037
0.8302	Intermediate Similarity	NPC224314
0.8302	Intermediate Similarity	NPC87998
0.8302	Intermediate Similarity	NPC23808
0.8302	Intermediate Similarity	NPC222202
0.8302	Intermediate Similarity	NPC269297
0.8302	Intermediate Similarity	NPC477811
0.83	Intermediate Similarity	NPC476893
0.8286	Intermediate Similarity	NPC476513
0.8283	Intermediate Similarity	NPC476894
0.8269	Intermediate Similarity	NPC474569
0.8265	Intermediate Similarity	NPC27531
0.8257	Intermediate Similarity	NPC63609
0.8252	Intermediate Similarity	NPC473198
0.8252	Intermediate Similarity	NPC213190
0.8241	Intermediate Similarity	NPC469348
0.8241	Intermediate Similarity	NPC469347
0.8241	Intermediate Similarity	NPC144068
0.8235	Intermediate Similarity	NPC267510
0.823	Intermediate Similarity	NPC202261
0.823	Intermediate Similarity	NPC295133
0.823	Intermediate Similarity	NPC106589
0.823	Intermediate Similarity	NPC257207
0.8224	Intermediate Similarity	NPC476547
0.8224	Intermediate Similarity	NPC13193
0.8224	Intermediate Similarity	NPC477028
0.8224	Intermediate Similarity	NPC124677
0.8224	Intermediate Similarity	NPC477032
0.8218	Intermediate Similarity	NPC476895
0.8218	Intermediate Similarity	NPC234287
0.8218	Intermediate Similarity	NPC280825
0.8211	Intermediate Similarity	NPC24277
0.8208	Intermediate Similarity	NPC472901
0.8208	Intermediate Similarity	NPC476835
0.8208	Intermediate Similarity	NPC473570
0.82	Intermediate Similarity	NPC304899
0.82	Intermediate Similarity	NPC253115
0.8191	Intermediate Similarity	NPC124172
0.819	Intermediate Similarity	NPC94272
0.8182	Intermediate Similarity	NPC20979
0.8182	Intermediate Similarity	NPC87250
0.8182	Intermediate Similarity	NPC142066
0.8182	Intermediate Similarity	NPC477807
0.8182	Intermediate Similarity	NPC471353
0.8182	Intermediate Similarity	NPC158344
0.8182	Intermediate Similarity	NPC473852
0.8182	Intermediate Similarity	NPC474418
0.8182	Intermediate Similarity	NPC243196
0.8182	Intermediate Similarity	NPC196429
0.8182	Intermediate Similarity	NPC100048
0.8182	Intermediate Similarity	NPC476690
0.8182	Intermediate Similarity	NPC471355
0.8182	Intermediate Similarity	NPC244402
0.8182	Intermediate Similarity	NPC471351
0.8182	Intermediate Similarity	NPC157376
0.8182	Intermediate Similarity	NPC99728
0.8182	Intermediate Similarity	NPC34390
0.8182	Intermediate Similarity	NPC309034
0.8182	Intermediate Similarity	NPC77319
0.8182	Intermediate Similarity	NPC50305

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 NPC176406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1810
0.2-0.3	4226
0.3-0.4	2009
0.4-0.5	467
0.5-0.6	206
0.6-0.7	191
0.7-0.8	40
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
0.8108	Intermediate Similarity	NPD7327	Approved
0.8108	Intermediate Similarity	NPD7328	Approved
0.8036	Intermediate Similarity	NPD7516	Approved
0.7895	Intermediate Similarity	NPD8380	Approved
0.7895	Intermediate Similarity	NPD8379	Approved
0.7895	Intermediate Similarity	NPD8378	Approved
0.7895	Intermediate Similarity	NPD8296	Approved
0.7895	Intermediate Similarity	NPD8335	Approved
0.7895	Intermediate Similarity	NPD8033	Approved
0.7807	Intermediate Similarity	NPD8294	Approved
0.7807	Intermediate Similarity	NPD8377	Approved
0.7685	Intermediate Similarity	NPD6412	Phase 2
0.7629	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7503	Approved
0.7579	Intermediate Similarity	NPD6928	Phase 2
0.7527	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6695	Phase 3
0.7524	Intermediate Similarity	NPD7638	Approved
0.7479	Intermediate Similarity	NPD7507	Approved
0.7453	Intermediate Similarity	NPD7640	Approved
0.7453	Intermediate Similarity	NPD7639	Approved
0.7438	Intermediate Similarity	NPD7319	Approved
0.7419	Intermediate Similarity	NPD6942	Approved
0.7419	Intermediate Similarity	NPD7339	Approved
0.74	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7525	Registered
0.735	Intermediate Similarity	NPD6054	Approved
0.735	Intermediate Similarity	NPD6059	Approved
0.7292	Intermediate Similarity	NPD6929	Approved
0.7228	Intermediate Similarity	NPD7524	Approved
0.7228	Intermediate Similarity	NPD7750	Discontinued
0.7227	Intermediate Similarity	NPD6370	Approved
0.7216	Intermediate Similarity	NPD6931	Approved
0.7216	Intermediate Similarity	NPD6930	Phase 2
0.7143	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD6015	Approved
0.7113	Intermediate Similarity	NPD7645	Phase 2
0.7107	Intermediate Similarity	NPD7492	Approved
0.7087	Intermediate Similarity	NPD6051	Approved
0.7083	Intermediate Similarity	NPD5988	Approved
0.7083	Intermediate Similarity	NPD5776	Phase 2
0.7083	Intermediate Similarity	NPD6925	Approved
0.7073	Intermediate Similarity	NPD7736	Approved
0.7049	Intermediate Similarity	NPD6616	Approved
0.7048	Intermediate Similarity	NPD8171	Discontinued
0.7048	Intermediate Similarity	NPD6399	Phase 3
0.7043	Intermediate Similarity	NPD6882	Approved
0.701	Intermediate Similarity	NPD7145	Approved
0.6992	Remote Similarity	NPD8293	Discontinued
0.6992	Remote Similarity	NPD7078	Approved
0.6991	Remote Similarity	NPD6686	Approved
0.6991	Remote Similarity	NPD7320	Approved
0.6984	Remote Similarity	NPD8449	Approved
0.6983	Remote Similarity	NPD8133	Approved
0.6964	Remote Similarity	NPD5739	Approved
0.6964	Remote Similarity	NPD6008	Approved
0.6964	Remote Similarity	NPD6675	Approved
0.6964	Remote Similarity	NPD6402	Approved
0.6964	Remote Similarity	NPD7128	Approved
0.6952	Remote Similarity	NPD7087	Discontinued
0.6947	Remote Similarity	NPD4785	Approved
0.6947	Remote Similarity	NPD4784	Approved
0.6931	Remote Similarity	NPD4786	Approved
0.6929	Remote Similarity	NPD8450	Suspended
0.6915	Remote Similarity	NPD4243	Approved
0.6907	Remote Similarity	NPD6932	Approved
0.6897	Remote Similarity	NPD6053	Discontinued
0.6885	Remote Similarity	NPD6067	Discontinued
0.6869	Remote Similarity	NPD7514	Phase 3
0.6863	Remote Similarity	NPD6893	Approved
0.6847	Remote Similarity	NPD7632	Discontinued
0.6842	Remote Similarity	NPD6881	Approved
0.6842	Remote Similarity	NPD6899	Approved
0.6807	Remote Similarity	NPD6009	Approved
0.68	Remote Similarity	NPD6033	Approved
0.68	Remote Similarity	NPD6902	Approved
0.6792	Remote Similarity	NPD7637	Suspended
0.6789	Remote Similarity	NPD6083	Phase 2
0.6789	Remote Similarity	NPD4755	Approved
0.6789	Remote Similarity	NPD6084	Phase 2
0.6783	Remote Similarity	NPD6373	Approved
0.6783	Remote Similarity	NPD6372	Approved
0.6771	Remote Similarity	NPD6924	Approved
0.6771	Remote Similarity	NPD6926	Approved
0.6768	Remote Similarity	NPD6683	Phase 2
0.6757	Remote Similarity	NPD4159	Approved
0.6754	Remote Similarity	NPD5697	Approved
0.6754	Remote Similarity	NPD5701	Approved
0.6733	Remote Similarity	NPD3667	Approved
0.6729	Remote Similarity	NPD4202	Approved
0.6724	Remote Similarity	NPD7102	Approved
0.6724	Remote Similarity	NPD7290	Approved
0.6724	Remote Similarity	NPD6883	Approved
0.67	Remote Similarity	NPD4748	Discontinued
0.67	Remote Similarity	NPD7332	Phase 2
0.6696	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6638	Remote Similarity	NPD6012	Approved
0.6638	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6014	Approved
0.6638	Remote Similarity	NPD6013	Approved
0.6634	Remote Similarity	NPD6898	Phase 1
0.6633	Remote Similarity	NPD6933	Approved
0.661	Remote Similarity	NPD8297	Approved
0.6606	Remote Similarity	NPD7991	Discontinued
0.6604	Remote Similarity	NPD4753	Phase 2
0.6604	Remote Similarity	NPD5328	Approved
0.6602	Remote Similarity	NPD3665	Phase 1
0.6602	Remote Similarity	NPD3133	Approved
0.6602	Remote Similarity	NPD3666	Approved
0.6579	Remote Similarity	NPD5141	Approved
0.6577	Remote Similarity	NPD4225	Approved
0.6562	Remote Similarity	NPD7150	Approved
0.6562	Remote Similarity	NPD7152	Approved
0.6562	Remote Similarity	NPD7151	Approved
0.6555	Remote Similarity	NPD4632	Approved
0.6552	Remote Similarity	NPD6011	Approved
0.6549	Remote Similarity	NPD4633	Approved
0.6549	Remote Similarity	NPD5226	Approved
0.6549	Remote Similarity	NPD5224	Approved
0.6549	Remote Similarity	NPD5225	Approved
0.6531	Remote Similarity	NPD5275	Approved
0.6531	Remote Similarity	NPD4190	Phase 3
0.6526	Remote Similarity	NPD6922	Approved
0.6526	Remote Similarity	NPD6923	Approved
0.6525	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6903	Approved
0.6509	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6319	Approved
0.6496	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5175	Approved
0.6491	Remote Similarity	NPD5174	Approved
0.6481	Remote Similarity	NPD8034	Phase 2
0.6481	Remote Similarity	NPD8035	Phase 2
0.6481	Remote Similarity	NPD6079	Approved
0.6476	Remote Similarity	NPD7146	Approved
0.6476	Remote Similarity	NPD5330	Approved
0.6476	Remote Similarity	NPD6684	Approved
0.6476	Remote Similarity	NPD6409	Approved
0.6476	Remote Similarity	NPD7521	Approved
0.6476	Remote Similarity	NPD7334	Approved
0.6476	Remote Similarity	NPD3618	Phase 1
0.646	Remote Similarity	NPD5223	Approved
0.6458	Remote Similarity	NPD7143	Approved
0.6458	Remote Similarity	NPD7144	Approved
0.6455	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5695	Phase 3
0.6441	Remote Similarity	NPD4634	Approved
0.6436	Remote Similarity	NPD4195	Approved
0.6435	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5956	Approved
0.6429	Remote Similarity	NPD5696	Approved
0.6415	Remote Similarity	NPD4250	Approved
0.6415	Remote Similarity	NPD4251	Approved
0.6393	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4768	Approved
0.6379	Remote Similarity	NPD4767	Approved
0.6373	Remote Similarity	NPD7509	Discontinued
0.6364	Remote Similarity	NPD7748	Approved
0.6349	Remote Similarity	NPD8328	Phase 3
0.6349	Remote Similarity	NPD7604	Phase 2
0.6348	Remote Similarity	NPD4754	Approved
0.6339	Remote Similarity	NPD7902	Approved
0.6331	Remote Similarity	NPD7625	Phase 1
0.633	Remote Similarity	NPD7515	Phase 2
0.633	Remote Similarity	NPD5693	Phase 1
0.6321	Remote Similarity	NPD4249	Approved
0.632	Remote Similarity	NPD8513	Phase 3
0.632	Remote Similarity	NPD8515	Approved
0.632	Remote Similarity	NPD5983	Phase 2
0.632	Remote Similarity	NPD8517	Approved
0.632	Remote Similarity	NPD8516	Approved
0.6316	Remote Similarity	NPD5344	Discontinued
0.6311	Remote Similarity	NPD6274	Approved
0.6306	Remote Similarity	NPD4629	Approved
0.6306	Remote Similarity	NPD5210	Approved
0.6303	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7101	Approved
0.629	Remote Similarity	NPD7100	Approved
0.6286	Remote Similarity	NPD3668	Phase 3
0.6286	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4729	Approved
0.6271	Remote Similarity	NPD4730	Approved
0.6271	Remote Similarity	NPD5128	Approved
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD4221	Approved
0.625	Remote Similarity	NPD5221	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