NPASS Compound

Structure

NPC22634 OpenBabel07101719252D 35 40 0 0 1 0 0 0 0 0999 V2000 1.7634 2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4975 -3.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4975 -3.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1314 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 -1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1939 2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3994 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 -2.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8635 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9975 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3994 0.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9894 0.5771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2654 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3994 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1314 -2.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8635 -2.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5823 0.7045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9067 1.7796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9975 -2.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1314 -1.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5334 0.3955 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5334 -0.6045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8849 1.5717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7295 -2.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.6931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8630 1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0759 0.1704 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 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 17 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 16 34 1 0 0 0 0 17 1 1 1 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 28 1 0 0 0 0 20 15 1 6 0 0 0 20 23 1 0 0 0 0 20 35 1 0 0 0 0 21 25 1 0 0 0 0 21 26 1 6 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 27 1 6 0 0 0 24 29 1 1 0 0 0 24 30 1 0 0 0 0 24 32 1 0 0 0 0 26 4 1 6 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 29 33 1 0 0 0 0 30 14 1 1 0 0 0 30 34 1 0 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	514.775
LogP:	5.237
LogD:	4.119
LogS:	-4.47
# Rotatable Bonds:	0
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	6.026
Fsp3:	0.867
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:	-4.993
MDCK Permeability:	3.0053415684960783e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.066
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	92.68567657470703%
Volume Distribution (VD):	1.209
Pgp-substrate:	5.44527530670166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.153
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.808

ADMET: Excretion

Clearance (CL):	5.434
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.598
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.946
Carcinogencity:	0.41
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC22634

Natural Product ID:	NPC22634
*Common Name:**	BDOVZLSMDAFYHY-SEJDCZPZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BDOVZLSMDAFYHY-SEJDCZPZSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-17-14-30(24(32)29(7,33)16-34-30)35-20-15-28(6)19-8-9-21-25(2,3)22(31)11-12-26(21,4)18(19)10-13-27(28,5)23(17)20/h8,10,17,20-24,31-33H,9,11-16H2,1-7H3/t17-,20+,21+,22+,23+,24-,26-,27-,28+,29+,30+/m1/s1
SMILES:	C[C@@H]1C[C@@]2([C@@H]([C@](C)(CO2)O)O)O[C@H]2C[C@@]3(C)C4=CC[C@H]5C(C)(C)[C@H](CC[C@]5(C)C4=CC[C@]3(C)[C@@H]12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375498
PubChem CID:	71713402
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
NPO33019	cimicifuga yunnanensis	Species	Ranunculaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[23621813]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1893	Cell Line	MEF	Mus musculus	IC50	=	6000.0	nM	PMID[491677]
NPT1893	Cell Line	MEF	Mus musculus	IC50	=	8600.0	nM	PMID[491677]

☑ 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 NPC22634 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	236
0.1-0.2	1545
0.2-0.3	5755
0.3-0.4	13929
0.4-0.5	9200
0.5-0.6	5853
0.6-0.7	4661
0.7-0.8	1416
0.8-0.85	79
0.85-0.9	17
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC275865
0.9286	High Similarity	NPC475701
0.9192	High Similarity	NPC471111
0.9192	High Similarity	NPC474464
0.91	High Similarity	NPC474015
0.8911	High Similarity	NPC26798
0.8889	High Similarity	NPC474022
0.8878	High Similarity	NPC216260
0.8878	High Similarity	NPC5358
0.8835	High Similarity	NPC128133
0.8835	High Similarity	NPC476835
0.8824	High Similarity	NPC226642
0.8776	High Similarity	NPC177818
0.8713	High Similarity	NPC213190
0.8687	High Similarity	NPC309493
0.8667	High Similarity	NPC208189
0.8667	High Similarity	NPC197231
0.8667	High Similarity	NPC65034
0.8627	High Similarity	NPC475365
0.86	High Similarity	NPC324598
0.8585	High Similarity	NPC19888
0.8585	High Similarity	NPC231797
0.8558	High Similarity	NPC476539
0.8558	High Similarity	NPC476540
0.8558	High Similarity	NPC476541
0.8558	High Similarity	NPC476538
0.8557	High Similarity	NPC235126
0.8557	High Similarity	NPC242419
0.8557	High Similarity	NPC98193
0.8544	High Similarity	NPC242748
0.8544	High Similarity	NPC181845
0.8515	High Similarity	NPC267510
0.8515	High Similarity	NPC4831
0.8515	High Similarity	NPC176406
0.8515	High Similarity	NPC47566
0.8515	High Similarity	NPC309425
0.8515	High Similarity	NPC472023
0.8515	High Similarity	NPC88000
0.8515	High Similarity	NPC129372
0.8515	High Similarity	NPC160734
0.8505	High Similarity	NPC178981
0.85	High Similarity	NPC234287
0.85	High Similarity	NPC280825
0.8476	Intermediate Similarity	NPC42482
0.8476	Intermediate Similarity	NPC477027
0.8476	Intermediate Similarity	NPC477026
0.8476	Intermediate Similarity	NPC40440
0.8476	Intermediate Similarity	NPC475670
0.8476	Intermediate Similarity	NPC70204
0.8476	Intermediate Similarity	NPC306131
0.8462	Intermediate Similarity	NPC305423
0.8462	Intermediate Similarity	NPC230507
0.8462	Intermediate Similarity	NPC470432
0.8462	Intermediate Similarity	NPC283829
0.8462	Intermediate Similarity	NPC113044
0.8462	Intermediate Similarity	NPC161676
0.8462	Intermediate Similarity	NPC14704
0.8447	Intermediate Similarity	NPC470885
0.8447	Intermediate Similarity	NPC187400
0.8447	Intermediate Similarity	NPC85593
0.8447	Intermediate Similarity	NPC221562
0.8447	Intermediate Similarity	NPC31430
0.8431	Intermediate Similarity	NPC136816
0.8426	Intermediate Similarity	NPC477810
0.8416	Intermediate Similarity	NPC471242
0.8416	Intermediate Similarity	NPC473200
0.8416	Intermediate Similarity	NPC7341
0.84	Intermediate Similarity	NPC473890
0.84	Intermediate Similarity	NPC243728
0.8396	Intermediate Similarity	NPC191439
0.8396	Intermediate Similarity	NPC103627
0.8396	Intermediate Similarity	NPC170974
0.8381	Intermediate Similarity	NPC98696
0.8381	Intermediate Similarity	NPC220427
0.8365	Intermediate Similarity	NPC474569
0.8365	Intermediate Similarity	NPC473923
0.8365	Intermediate Similarity	NPC473476
0.835	Intermediate Similarity	NPC472252
0.835	Intermediate Similarity	NPC114874
0.835	Intermediate Similarity	NPC131479
0.835	Intermediate Similarity	NPC245280
0.835	Intermediate Similarity	NPC189852
0.835	Intermediate Similarity	NPC157659
0.835	Intermediate Similarity	NPC211879
0.835	Intermediate Similarity	NPC155010
0.835	Intermediate Similarity	NPC473020
0.835	Intermediate Similarity	NPC31907
0.835	Intermediate Similarity	NPC8039
0.835	Intermediate Similarity	NPC120123
0.835	Intermediate Similarity	NPC286969
0.835	Intermediate Similarity	NPC16520
0.8349	Intermediate Similarity	NPC212660
0.8333	Intermediate Similarity	NPC144068
0.8333	Intermediate Similarity	NPC73385
0.8333	Intermediate Similarity	NPC476693
0.8318	Intermediate Similarity	NPC294129
0.8318	Intermediate Similarity	NPC13190
0.8318	Intermediate Similarity	NPC124677
0.8318	Intermediate Similarity	NPC476547
0.8318	Intermediate Similarity	NPC477028
0.8318	Intermediate Similarity	NPC477032
0.8318	Intermediate Similarity	NPC475247
0.8317	Intermediate Similarity	NPC158088
0.8317	Intermediate Similarity	NPC476895
0.8302	Intermediate Similarity	NPC232054
0.8302	Intermediate Similarity	NPC84956
0.8302	Intermediate Similarity	NPC244086
0.8302	Intermediate Similarity	NPC102016
0.8302	Intermediate Similarity	NPC46190
0.8302	Intermediate Similarity	NPC224098
0.8302	Intermediate Similarity	NPC6806
0.8302	Intermediate Similarity	NPC470433
0.8302	Intermediate Similarity	NPC95051
0.8302	Intermediate Similarity	NPC248746
0.8302	Intermediate Similarity	NPC14630
0.8302	Intermediate Similarity	NPC73243
0.8302	Intermediate Similarity	NPC473318
0.8302	Intermediate Similarity	NPC218571
0.8302	Intermediate Similarity	NPC208383
0.8302	Intermediate Similarity	NPC150372
0.8302	Intermediate Similarity	NPC250089
0.8302	Intermediate Similarity	NPC473328
0.8302	Intermediate Similarity	NPC28844
0.8302	Intermediate Similarity	NPC157530
0.8302	Intermediate Similarity	NPC475550
0.8302	Intermediate Similarity	NPC194207
0.8302	Intermediate Similarity	NPC477809
0.8302	Intermediate Similarity	NPC171073
0.8302	Intermediate Similarity	NPC309278
0.8302	Intermediate Similarity	NPC475333
0.8302	Intermediate Similarity	NPC300557
0.8302	Intermediate Similarity	NPC249265
0.8302	Intermediate Similarity	NPC22779
0.83	Intermediate Similarity	NPC207617
0.8286	Intermediate Similarity	NPC473469
0.8286	Intermediate Similarity	NPC190395
0.8283	Intermediate Similarity	NPC305160
0.8269	Intermediate Similarity	NPC165033
0.8269	Intermediate Similarity	NPC312774
0.8269	Intermediate Similarity	NPC75608
0.8269	Intermediate Similarity	NPC273879
0.8265	Intermediate Similarity	NPC210268
0.8257	Intermediate Similarity	NPC167183
0.8257	Intermediate Similarity	NPC32707
0.8252	Intermediate Similarity	NPC312553
0.8252	Intermediate Similarity	NPC68630
0.8252	Intermediate Similarity	NPC159036
0.8252	Intermediate Similarity	NPC288694
0.8252	Intermediate Similarity	NPC228049
0.8252	Intermediate Similarity	NPC52585
0.8241	Intermediate Similarity	NPC112274
0.8241	Intermediate Similarity	NPC32361
0.8241	Intermediate Similarity	NPC477050
0.8241	Intermediate Similarity	NPC244431
0.8241	Intermediate Similarity	NPC473567
0.8241	Intermediate Similarity	NPC263359
0.8241	Intermediate Similarity	NPC31896
0.8241	Intermediate Similarity	NPC216595
0.8241	Intermediate Similarity	NPC254255
0.8241	Intermediate Similarity	NPC210569
0.8235	Intermediate Similarity	NPC282669
0.8235	Intermediate Similarity	NPC473790
0.8224	Intermediate Similarity	NPC269297
0.8224	Intermediate Similarity	NPC224314
0.8224	Intermediate Similarity	NPC222202
0.8224	Intermediate Similarity	NPC23808
0.8224	Intermediate Similarity	NPC65155
0.8224	Intermediate Similarity	NPC247037
0.8224	Intermediate Similarity	NPC87998
0.8224	Intermediate Similarity	NPC477811
0.8224	Intermediate Similarity	NPC141433
0.8218	Intermediate Similarity	NPC76486
0.8218	Intermediate Similarity	NPC476893
0.8208	Intermediate Similarity	NPC7213
0.8191	Intermediate Similarity	NPC132635
0.819	Intermediate Similarity	NPC309448
0.819	Intermediate Similarity	NPC160816
0.819	Intermediate Similarity	NPC269627
0.819	Intermediate Similarity	NPC152584
0.819	Intermediate Similarity	NPC472898
0.819	Intermediate Similarity	NPC472900
0.819	Intermediate Similarity	NPC208594
0.819	Intermediate Similarity	NPC127801
0.819	Intermediate Similarity	NPC69737
0.819	Intermediate Similarity	NPC473199
0.819	Intermediate Similarity	NPC194842
0.819	Intermediate Similarity	NPC472899
0.819	Intermediate Similarity	NPC208477
0.8173	Intermediate Similarity	NPC471450
0.8173	Intermediate Similarity	NPC473198
0.8173	Intermediate Similarity	NPC99627
0.8173	Intermediate Similarity	NPC16573
0.8173	Intermediate Similarity	NPC473129
0.8165	Intermediate Similarity	NPC51154
0.8165	Intermediate Similarity	NPC79900
0.8165	Intermediate Similarity	NPC476671
0.8163	Intermediate Similarity	NPC107189
0.8155	Intermediate Similarity	NPC470434
0.8155	Intermediate Similarity	NPC470054
0.8155	Intermediate Similarity	NPC476896

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 NPC22634 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	1726
0.2-0.3	4390
0.3-0.4	1939
0.4-0.5	467
0.5-0.6	210
0.6-0.7	180
0.7-0.8	37
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
0.7876	Intermediate Similarity	NPD7328	Approved
0.7876	Intermediate Similarity	NPD7327	Approved
0.7826	Intermediate Similarity	NPD7503	Approved
0.7807	Intermediate Similarity	NPD7516	Approved
0.7778	Intermediate Similarity	NPD6412	Phase 2
0.7739	Intermediate Similarity	NPD8377	Approved
0.7739	Intermediate Similarity	NPD8294	Approved
0.7672	Intermediate Similarity	NPD8379	Approved
0.7672	Intermediate Similarity	NPD8033	Approved
0.7672	Intermediate Similarity	NPD8296	Approved
0.7672	Intermediate Similarity	NPD8380	Approved
0.7672	Intermediate Similarity	NPD8335	Approved
0.7672	Intermediate Similarity	NPD8378	Approved
0.7586	Intermediate Similarity	NPD6059	Approved
0.7586	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD6928	Phase 2
0.7476	Intermediate Similarity	NPD8171	Discontinued
0.7458	Intermediate Similarity	NPD6370	Approved
0.7417	Intermediate Similarity	NPD7507	Approved
0.7373	Intermediate Similarity	NPD6015	Approved
0.7373	Intermediate Similarity	NPD6016	Approved
0.7333	Intermediate Similarity	NPD7492	Approved
0.7327	Intermediate Similarity	NPD7524	Approved
0.732	Intermediate Similarity	NPD7525	Registered
0.7311	Intermediate Similarity	NPD5988	Approved
0.7295	Intermediate Similarity	NPD7736	Approved
0.7273	Intermediate Similarity	NPD6616	Approved
0.7236	Intermediate Similarity	NPD7319	Approved
0.7213	Intermediate Similarity	NPD7078	Approved
0.7213	Intermediate Similarity	NPD8293	Discontinued
0.72	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6695	Phase 3
0.7034	Intermediate Similarity	NPD6009	Approved
0.7016	Intermediate Similarity	NPD6033	Approved
0.6983	Remote Similarity	NPD6882	Approved
0.697	Remote Similarity	NPD4748	Discontinued
0.6967	Remote Similarity	NPD6067	Discontinued
0.693	Remote Similarity	NPD7320	Approved
0.6929	Remote Similarity	NPD8449	Approved
0.6923	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.6907	Remote Similarity	NPD6933	Approved
0.6907	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5739	Approved
0.6903	Remote Similarity	NPD6675	Approved
0.6903	Remote Similarity	NPD7128	Approved
0.6903	Remote Similarity	NPD6402	Approved
0.6875	Remote Similarity	NPD8450	Suspended
0.6869	Remote Similarity	NPD7645	Phase 2
0.686	Remote Similarity	NPD6319	Approved
0.6838	Remote Similarity	NPD8297	Approved
0.6827	Remote Similarity	NPD7750	Discontinued
0.6827	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7638	Approved
0.6814	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7339	Approved
0.6804	Remote Similarity	NPD6942	Approved
0.68	Remote Similarity	NPD6930	Phase 2
0.68	Remote Similarity	NPD6931	Approved
0.6783	Remote Similarity	NPD6881	Approved
0.6783	Remote Similarity	NPD6899	Approved
0.6757	Remote Similarity	NPD7640	Approved
0.6757	Remote Similarity	NPD7639	Approved
0.6754	Remote Similarity	NPD6008	Approved
0.6727	Remote Similarity	NPD4755	Approved
0.6724	Remote Similarity	NPD6373	Approved
0.6724	Remote Similarity	NPD6372	Approved
0.6701	Remote Similarity	NPD6924	Approved
0.6701	Remote Similarity	NPD6926	Approved
0.67	Remote Similarity	NPD6929	Approved
0.6696	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6638	Remote Similarity	NPD6686	Approved
0.6612	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.661	Remote Similarity	NPD8130	Phase 1
0.661	Remote Similarity	NPD6617	Approved
0.661	Remote Similarity	NPD6649	Approved
0.661	Remote Similarity	NPD6869	Approved
0.661	Remote Similarity	NPD6650	Approved
0.661	Remote Similarity	NPD6847	Approved
0.6607	Remote Similarity	NPD4700	Approved
0.6607	Remote Similarity	NPD4696	Approved
0.6607	Remote Similarity	NPD5286	Approved
0.6607	Remote Similarity	NPD5285	Approved
0.6581	Remote Similarity	NPD6014	Approved
0.6581	Remote Similarity	NPD6013	Approved
0.6581	Remote Similarity	NPD6012	Approved
0.6577	Remote Similarity	NPD6083	Phase 2
0.6577	Remote Similarity	NPD6084	Phase 2
0.6574	Remote Similarity	NPD7087	Discontinued
0.656	Remote Similarity	NPD8328	Phase 3
0.656	Remote Similarity	NPD7604	Phase 2
0.6549	Remote Similarity	NPD4159	Approved
0.6545	Remote Similarity	NPD5695	Phase 3
0.6545	Remote Similarity	NPD7991	Discontinued
0.6535	Remote Similarity	NPD6683	Phase 2
0.6532	Remote Similarity	NPD8516	Approved
0.6532	Remote Similarity	NPD8515	Approved
0.6532	Remote Similarity	NPD5983	Phase 2
0.6532	Remote Similarity	NPD8513	Phase 3
0.6532	Remote Similarity	NPD8517	Approved
0.6531	Remote Similarity	NPD4785	Approved
0.6531	Remote Similarity	NPD4784	Approved
0.6514	Remote Similarity	NPD6399	Phase 3
0.6512	Remote Similarity	NPD5956	Approved
0.65	Remote Similarity	NPD5776	Phase 2
0.65	Remote Similarity	NPD6925	Approved
0.6496	Remote Similarity	NPD6011	Approved
0.6491	Remote Similarity	NPD5226	Approved
0.6491	Remote Similarity	NPD5211	Phase 2
0.6491	Remote Similarity	NPD4633	Approved
0.6491	Remote Similarity	NPD5224	Approved
0.6491	Remote Similarity	NPD5225	Approved
0.6476	Remote Similarity	NPD6893	Approved
0.6475	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD7514	Phase 3
0.6471	Remote Similarity	NPD7509	Discontinued
0.6471	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6336	Discontinued
0.6441	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7145	Approved
0.6435	Remote Similarity	NPD5175	Approved
0.6435	Remote Similarity	NPD5174	Approved
0.6422	Remote Similarity	NPD5284	Approved
0.6422	Remote Similarity	NPD5281	Approved
0.6404	Remote Similarity	NPD5223	Approved
0.6396	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4753	Phase 2
0.6389	Remote Similarity	NPD6051	Approved
0.6389	Remote Similarity	NPD5328	Approved
0.6381	Remote Similarity	NPD4786	Approved
0.6379	Remote Similarity	NPD5141	Approved
0.6348	Remote Similarity	NPD7632	Discontinued
0.633	Remote Similarity	NPD5207	Approved
0.633	Remote Similarity	NPD3168	Discontinued
0.6327	Remote Similarity	NPD7151	Approved
0.6327	Remote Similarity	NPD7152	Approved
0.6327	Remote Similarity	NPD7150	Approved
0.6325	Remote Similarity	NPD4767	Approved
0.6325	Remote Similarity	NPD4768	Approved
0.6311	Remote Similarity	NPD7332	Phase 2
0.63	Remote Similarity	NPD5275	Approved
0.63	Remote Similarity	NPD4190	Phase 3
0.6293	Remote Similarity	NPD4754	Approved
0.6289	Remote Similarity	NPD6922	Approved
0.6289	Remote Similarity	NPD6923	Approved
0.6286	Remote Similarity	NPD7625	Phase 1
0.6281	Remote Similarity	NPD6053	Discontinued
0.6273	Remote Similarity	NPD8034	Phase 2
0.6273	Remote Similarity	NPD7637	Suspended
0.6273	Remote Similarity	NPD6411	Approved
0.6273	Remote Similarity	NPD6079	Approved
0.6273	Remote Similarity	NPD8035	Phase 2
0.6273	Remote Similarity	NPD6050	Approved
0.6262	Remote Similarity	NPD5279	Phase 3
0.6262	Remote Similarity	NPD4694	Approved
0.6262	Remote Similarity	NPD5280	Approved
0.6262	Remote Similarity	NPD3618	Phase 1
0.626	Remote Similarity	NPD6274	Approved
0.625	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD6898	Phase 1
0.624	Remote Similarity	NPD7100	Approved
0.624	Remote Similarity	NPD7101	Approved
0.6228	Remote Similarity	NPD4225	Approved
0.6228	Remote Similarity	NPD5696	Approved
0.6226	Remote Similarity	NPD3665	Phase 1
0.6226	Remote Similarity	NPD3133	Approved
0.6226	Remote Similarity	NPD3666	Approved
0.6224	Remote Similarity	NPD7143	Approved
0.6224	Remote Similarity	NPD7144	Approved
0.6218	Remote Similarity	NPD4730	Approved
0.6218	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4729	Approved
0.6218	Remote Similarity	NPD5128	Approved
0.6214	Remote Similarity	NPD4195	Approved
0.62	Remote Similarity	NPD1811	Approved
0.62	Remote Similarity	NPD1810	Approved
0.619	Remote Similarity	NPD3667	Approved
0.6182	Remote Similarity	NPD5692	Phase 3
0.6168	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7748	Approved
0.616	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD8074	Phase 3
0.6147	Remote Similarity	NPD6903	Approved
0.6147	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6908	Approved
0.6142	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6909	Approved
0.614	Remote Similarity	NPD7902	Approved
0.6139	Remote Similarity	NPD8264	Approved
0.6126	Remote Similarity	NPD7515	Phase 2

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