NPASS Compound

Structure

NPC471180 OpenBabel07101718202D 33 36 0 0 1 0 0 0 0 0999 V2000 2.4925 3.6207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3099 4.8033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3108 -0.5313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8421 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9474 -1.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4211 -0.8204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6173 2.3108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4903 3.7318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7686 2.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6173 3.2581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9474 3.9280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9474 1.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6699 3.2581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3108 3.2581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6699 2.3108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4211 0.8204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.9280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3108 2.3108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4903 1.8371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4737 0.8204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9474 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3684 0.8204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3625 4.8033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8421 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8421 1.6409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4903 -0.0576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3684 0.8204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4211 -0.8204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4737 -0.8204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2118 3.5509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2118 2.0180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 10 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 32 1 0 0 0 0 9 33 1 0 0 0 0 10 1 1 6 0 0 0 10 11 1 0 0 0 0 11 2 1 6 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 32 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 25 1 6 0 0 0 19 20 1 0 0 0 0 19 33 1 0 0 0 0 20 28 1 0 0 0 0 21 23 2 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.17
Volume:	450.091
LogP:	3.259
LogD:	1.982
LogS:	-2.912
# Rotatable Bonds:	5
TPSA:	112.91
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	4.02
Fsp3:	0.458
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:	-5.25
MDCK Permeability:	1.303523822571151e-05
Pgp-inhibitor:	0.301
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	87.03292083740234%
Volume Distribution (VD):	0.738
Pgp-substrate:	9.033679008483887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.075
CYP2C9-substrate:	0.637
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	1.976
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.286
Human Hepatotoxicity (H-HT):	0.381
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.389
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.032
Carcinogencity:	0.084
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.277

Download Data

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

Natural Product: NPC471180

Natural Product ID:	NPC471180
*Common Name:**	TZBMJQDKFVLNJT-PJYBLOJUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TZBMJQDKFVLNJT-PJYBLOJUSA-N
Standard InCHI:	InChI=1S/C24H28O9/c1-10-7-12-15(21(29-4)23(31-6)22(30-5)17(12)24(26)27)16-13(18(25)11(10)2)8-14-19(20(16)28-3)33-9-32-14/h8,10-11,18,25H,7,9H2,1-6H3,(H,26,27)/t10-,11-,18-/m1/s1
SMILES:	CC1CC2=C(C3=C(C4=C(C=C3C(C1C)O)OCO4)OC)C(=C(C(=C2C(=O)O)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386329
PubChem CID:	71726086
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	Stems	Luoji Mountain Village, Xichang County, Sicuan Province, China	2011-Sep	PMID[23738539]
NPO29191	Schisandra neglecta	Species	Schisandraceae	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
EC50	1
IC50	5
Others	2

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	>	10000.0	nM	PMID[460942]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	86700.0	nM	PMID[460942]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7400.0	nM	PMID[460942]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6800.0	nM	PMID[460942]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[460942]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	2200.0	nM	PMID[460942]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	40.3	n.a.	PMID[460942]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[460942]

☑ 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 NPC471180 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	371
0.1-0.2	1522
0.2-0.3	3409
0.3-0.4	7830
0.4-0.5	10467
0.5-0.6	4064
0.6-0.7	5305
0.7-0.8	7451
0.8-0.85	1989
0.85-0.9	279
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9812	High Similarity	NPC471181
0.9317	High Similarity	NPC475865
0.925	High Similarity	NPC474770
0.9198	High Similarity	NPC469518
0.9198	High Similarity	NPC469475
0.9187	High Similarity	NPC325122
0.9096	High Similarity	NPC178737
0.9096	High Similarity	NPC469506
0.9042	High Similarity	NPC477881
0.9018	High Similarity	NPC61141
0.8994	High Similarity	NPC474514
0.8944	High Similarity	NPC477380
0.8944	High Similarity	NPC301897
0.8931	High Similarity	NPC220577
0.8922	High Similarity	NPC477883
0.8916	High Similarity	NPC311912
0.8902	High Similarity	NPC125991
0.8902	High Similarity	NPC469512
0.8889	High Similarity	NPC84935
0.8889	High Similarity	NPC77679
0.8889	High Similarity	NPC477885
0.8889	High Similarity	NPC190020
0.8882	High Similarity	NPC477882
0.8882	High Similarity	NPC477880
0.8875	High Similarity	NPC24562
0.8875	High Similarity	NPC245948
0.8862	High Similarity	NPC88557
0.8855	High Similarity	NPC118162
0.8855	High Similarity	NPC83049
0.8855	High Similarity	NPC320471
0.8855	High Similarity	NPC474042
0.8855	High Similarity	NPC174734
0.8827	High Similarity	NPC150227
0.882	High Similarity	NPC312763
0.882	High Similarity	NPC348849
0.882	High Similarity	NPC178195
0.8812	High Similarity	NPC104353
0.881	High Similarity	NPC17219
0.8802	High Similarity	NPC79322
0.8797	High Similarity	NPC316676
0.8797	High Similarity	NPC325720
0.8797	High Similarity	NPC304821
0.8795	High Similarity	NPC477884
0.878	High Similarity	NPC47623
0.878	High Similarity	NPC470358
0.8773	High Similarity	NPC19947
0.8773	High Similarity	NPC207584
0.8765	High Similarity	NPC79998
0.8765	High Similarity	NPC199926
0.8765	High Similarity	NPC16082
0.8765	High Similarity	NPC82592
0.8765	High Similarity	NPC238834
0.875	High Similarity	NPC303519
0.875	High Similarity	NPC234152
0.875	High Similarity	NPC117911
0.8743	High Similarity	NPC472452
0.8727	High Similarity	NPC319749
0.8727	High Similarity	NPC258322
0.8727	High Similarity	NPC103201
0.8727	High Similarity	NPC473106
0.8727	High Similarity	NPC191352
0.8721	High Similarity	NPC329161
0.8721	High Similarity	NPC470091
0.8721	High Similarity	NPC240887
0.872	High Similarity	NPC279732
0.872	High Similarity	NPC125713
0.8713	High Similarity	NPC196771
0.8712	High Similarity	NPC469474
0.8712	High Similarity	NPC237946
0.8712	High Similarity	NPC32373
0.8712	High Similarity	NPC473323
0.8704	High Similarity	NPC473425
0.8704	High Similarity	NPC281477
0.8698	High Similarity	NPC477572
0.8698	High Similarity	NPC477571
0.8698	High Similarity	NPC477573
0.8696	High Similarity	NPC56184
0.8696	High Similarity	NPC200773
0.8696	High Similarity	NPC240768
0.8688	High Similarity	NPC473989
0.8683	High Similarity	NPC475738
0.8675	High Similarity	NPC76687
0.8675	High Similarity	NPC280778
0.8675	High Similarity	NPC469575
0.8675	High Similarity	NPC474763
0.8675	High Similarity	NPC144843
0.8671	High Similarity	NPC170203
0.8667	High Similarity	NPC292415
0.8667	High Similarity	NPC472055
0.8659	High Similarity	NPC167595
0.8655	High Similarity	NPC199533
0.8655	High Similarity	NPC470454
0.8655	High Similarity	NPC146803
0.865	High Similarity	NPC476065
0.865	High Similarity	NPC478238
0.8647	High Similarity	NPC38438
0.8647	High Similarity	NPC223375
0.8647	High Similarity	NPC475825
0.8642	High Similarity	NPC77237
0.8642	High Similarity	NPC53669
0.8642	High Similarity	NPC308739
0.8642	High Similarity	NPC474606
0.8642	High Similarity	NPC126405
0.8642	High Similarity	NPC475116
0.8642	High Similarity	NPC217708
0.8642	High Similarity	NPC16791
0.8642	High Similarity	NPC297271
0.8639	High Similarity	NPC473202
0.8634	High Similarity	NPC119929
0.8634	High Similarity	NPC96501
0.8634	High Similarity	NPC179178
0.8634	High Similarity	NPC224472
0.8634	High Similarity	NPC475756
0.8634	High Similarity	NPC62354
0.8631	High Similarity	NPC178851
0.8631	High Similarity	NPC329119
0.8631	High Similarity	NPC20216
0.8625	High Similarity	NPC477698
0.8623	High Similarity	NPC474350
0.8614	High Similarity	NPC474779
0.8614	High Similarity	NPC209411
0.8614	High Similarity	NPC239890
0.8614	High Similarity	NPC288149
0.8614	High Similarity	NPC349525
0.8613	High Similarity	NPC212290
0.8608	High Similarity	NPC27106
0.8606	High Similarity	NPC215375
0.8606	High Similarity	NPC45846
0.8606	High Similarity	NPC62518
0.8606	High Similarity	NPC470339
0.8606	High Similarity	NPC474043
0.8606	High Similarity	NPC315157
0.8605	High Similarity	NPC473713
0.8599	High Similarity	NPC324962
0.8598	High Similarity	NPC54928
0.8598	High Similarity	NPC227062
0.8598	High Similarity	NPC155063
0.8598	High Similarity	NPC109765
0.8596	High Similarity	NPC98776
0.8589	High Similarity	NPC273578
0.8589	High Similarity	NPC198461
0.8589	High Similarity	NPC57211
0.8589	High Similarity	NPC287504
0.8589	High Similarity	NPC136757
0.8588	High Similarity	NPC298778
0.8588	High Similarity	NPC212748
0.858	High Similarity	NPC473732
0.858	High Similarity	NPC473094
0.858	High Similarity	NPC298847
0.858	High Similarity	NPC272566
0.858	High Similarity	NPC471154
0.858	High Similarity	NPC116745
0.858	High Similarity	NPC477502
0.858	High Similarity	NPC215921
0.858	High Similarity	NPC151425
0.858	High Similarity	NPC70016
0.8571	High Similarity	NPC25361
0.8571	High Similarity	NPC316989
0.8571	High Similarity	NPC327652
0.8571	High Similarity	NPC474301
0.8571	High Similarity	NPC7752
0.8571	High Similarity	NPC326520
0.8571	High Similarity	NPC112981
0.8563	High Similarity	NPC116838
0.8563	High Similarity	NPC208797
0.8563	High Similarity	NPC249070
0.8563	High Similarity	NPC22324
0.8563	High Similarity	NPC53680
0.8563	High Similarity	NPC215612
0.8563	High Similarity	NPC22130
0.8562	High Similarity	NPC198129
0.8562	High Similarity	NPC477375
0.8562	High Similarity	NPC252281
0.8562	High Similarity	NPC327352
0.8555	High Similarity	NPC469600
0.8554	High Similarity	NPC239818
0.8554	High Similarity	NPC200594
0.8554	High Similarity	NPC96593
0.8554	High Similarity	NPC78944
0.8554	High Similarity	NPC91634
0.8554	High Similarity	NPC218471
0.8554	High Similarity	NPC150943
0.8554	High Similarity	NPC268718
0.8554	High Similarity	NPC24627
0.8554	High Similarity	NPC119910
0.8553	High Similarity	NPC321696
0.8553	High Similarity	NPC321958
0.8547	High Similarity	NPC63105
0.8547	High Similarity	NPC474345
0.8547	High Similarity	NPC469601
0.8547	High Similarity	NPC68381
0.8547	High Similarity	NPC472607
0.8545	High Similarity	NPC475592
0.8545	High Similarity	NPC202495
0.8545	High Similarity	NPC474990
0.8544	High Similarity	NPC143092
0.8544	High Similarity	NPC18211
0.8544	High Similarity	NPC474036
0.8538	High Similarity	NPC472386
0.8538	High Similarity	NPC260263

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 NPC471180 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	930
0.2-0.3	1881
0.3-0.4	2607
0.4-0.5	1860
0.5-0.6	971
0.6-0.7	409
0.7-0.8	143
0.8-0.85	26
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8875	High Similarity	NPD37	Approved
0.8788	High Similarity	NPD6232	Discontinued
0.8743	High Similarity	NPD7473	Discontinued
0.8712	High Similarity	NPD4967	Phase 2
0.8712	High Similarity	NPD4965	Approved
0.8712	High Similarity	NPD4966	Approved
0.858	High Similarity	NPD3818	Discontinued
0.8494	Intermediate Similarity	NPD6234	Discontinued
0.8323	Intermediate Similarity	NPD2533	Approved
0.8323	Intermediate Similarity	NPD2534	Approved
0.8323	Intermediate Similarity	NPD2532	Approved
0.8314	Intermediate Similarity	NPD5844	Phase 1
0.8284	Intermediate Similarity	NPD7199	Phase 2
0.8266	Intermediate Similarity	NPD7074	Phase 3
0.8256	Intermediate Similarity	NPD7228	Approved
0.8229	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD5494	Approved
0.8221	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD7054	Approved
0.8171	Intermediate Similarity	NPD6559	Discontinued
0.8161	Intermediate Similarity	NPD7472	Approved
0.8144	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD3817	Phase 2
0.8084	Intermediate Similarity	NPD1934	Approved
0.8081	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD3882	Suspended
0.8047	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7808	Phase 3
0.8011	Intermediate Similarity	NPD6797	Phase 2
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD7240	Approved
0.7966	Intermediate Similarity	NPD7251	Discontinued
0.7964	Intermediate Similarity	NPD4380	Phase 2
0.7956	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6166	Phase 2
0.7931	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1465	Phase 2
0.7929	Intermediate Similarity	NPD2801	Approved
0.7927	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7075	Discontinued
0.787	Intermediate Similarity	NPD6801	Discontinued
0.7869	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6959	Discontinued
0.7849	Intermediate Similarity	NPD919	Approved
0.7824	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD8151	Discontinued
0.7716	Intermediate Similarity	NPD2935	Discontinued
0.7714	Intermediate Similarity	NPD5711	Approved
0.7714	Intermediate Similarity	NPD5710	Approved
0.7706	Intermediate Similarity	NPD7411	Suspended
0.768	Intermediate Similarity	NPD8313	Approved
0.768	Intermediate Similarity	NPD8312	Approved
0.7674	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD3926	Phase 2
0.7667	Intermediate Similarity	NPD7685	Pre-registration
0.7665	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD1247	Approved
0.7636	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1511	Approved
0.7605	Intermediate Similarity	NPD6799	Approved
0.7586	Intermediate Similarity	NPD3749	Approved
0.7574	Intermediate Similarity	NPD920	Approved
0.7572	Intermediate Similarity	NPD5402	Approved
0.7554	Intermediate Similarity	NPD8434	Phase 2
0.7546	Intermediate Similarity	NPD1510	Phase 2
0.7544	Intermediate Similarity	NPD6599	Discontinued
0.7529	Intermediate Similarity	NPD7768	Phase 2
0.7528	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1240	Approved
0.7515	Intermediate Similarity	NPD1512	Approved
0.7514	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD3226	Approved
0.7485	Intermediate Similarity	NPD7458	Discontinued
0.747	Intermediate Similarity	NPD1243	Approved
0.747	Intermediate Similarity	NPD2800	Approved
0.7469	Intermediate Similarity	NPD230	Phase 1
0.7461	Intermediate Similarity	NPD7435	Discontinued
0.7456	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3751	Discontinued
0.7435	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4628	Phase 3
0.7423	Intermediate Similarity	NPD1607	Approved
0.7416	Intermediate Similarity	NPD3787	Discontinued
0.741	Intermediate Similarity	NPD1549	Phase 2
0.7409	Intermediate Similarity	NPD5006	Approved
0.7409	Intermediate Similarity	NPD5005	Approved
0.7396	Intermediate Similarity	NPD6776	Approved
0.7396	Intermediate Similarity	NPD7390	Discontinued
0.7396	Intermediate Similarity	NPD6782	Approved
0.7396	Intermediate Similarity	NPD6777	Approved
0.7396	Intermediate Similarity	NPD6779	Approved
0.7396	Intermediate Similarity	NPD6780	Approved
0.7396	Intermediate Similarity	NPD6781	Approved
0.7396	Intermediate Similarity	NPD6778	Approved
0.7394	Intermediate Similarity	NPD2796	Approved
0.7374	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7783	Phase 2
0.7368	Intermediate Similarity	NPD5403	Approved
0.7362	Intermediate Similarity	NPD447	Suspended
0.7353	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7930	Approved
0.7337	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD3027	Phase 3
0.7326	Intermediate Similarity	NPD1653	Approved
0.7321	Intermediate Similarity	NPD3750	Approved
0.7317	Intermediate Similarity	NPD6651	Approved
0.7314	Intermediate Similarity	NPD8455	Phase 2
0.7301	Intermediate Similarity	NPD943	Approved
0.7292	Intermediate Similarity	NPD4420	Approved
0.7284	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7696	Phase 3
0.7282	Intermediate Similarity	NPD7698	Approved
0.7282	Intermediate Similarity	NPD7697	Approved
0.7282	Intermediate Similarity	NPD7680	Approved
0.7278	Intermediate Similarity	NPD5242	Approved
0.7273	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD8150	Discontinued
0.7262	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1933	Approved
0.7251	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5401	Approved
0.7246	Intermediate Similarity	NPD2346	Discontinued
0.7245	Intermediate Similarity	NPD7870	Phase 2
0.7245	Intermediate Similarity	NPD7871	Phase 2
0.7236	Intermediate Similarity	NPD7874	Approved
0.7236	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5953	Discontinued
0.7216	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1551	Phase 2
0.7186	Intermediate Similarity	NPD2438	Suspended
0.7176	Intermediate Similarity	NPD6190	Approved
0.7167	Intermediate Similarity	NPD8127	Discontinued
0.716	Intermediate Similarity	NPD6674	Discontinued
0.7157	Intermediate Similarity	NPD8320	Phase 1
0.7157	Intermediate Similarity	NPD8319	Approved
0.7152	Intermediate Similarity	NPD3705	Approved
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7136	Intermediate Similarity	NPD7701	Phase 2
0.7135	Intermediate Similarity	NPD6535	Approved
0.7135	Intermediate Similarity	NPD6534	Approved
0.7126	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3748	Approved
0.7125	Intermediate Similarity	NPD1283	Approved
0.712	Intermediate Similarity	NPD7286	Phase 2
0.7118	Intermediate Similarity	NPD7003	Approved
0.7114	Intermediate Similarity	NPD7801	Approved
0.7083	Intermediate Similarity	NPD5405	Approved
0.7083	Intermediate Similarity	NPD5408	Approved
0.7083	Intermediate Similarity	NPD5404	Approved
0.7083	Intermediate Similarity	NPD5406	Approved
0.7045	Intermediate Similarity	NPD7028	Phase 2
0.7041	Intermediate Similarity	NPD2344	Approved
0.7041	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7266	Discontinued
0.7037	Intermediate Similarity	NPD2798	Approved
0.7026	Intermediate Similarity	NPD7699	Phase 2
0.7026	Intermediate Similarity	NPD7700	Phase 2
0.7024	Intermediate Similarity	NPD7033	Discontinued
0.7018	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6273	Approved
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6385	Approved
0.7006	Intermediate Similarity	NPD6386	Approved
0.6988	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2979	Phase 3
0.6988	Remote Similarity	NPD4060	Phase 1
0.6988	Remote Similarity	NPD1613	Approved
0.697	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2313	Discontinued
0.697	Remote Similarity	NPD3764	Approved
0.6962	Remote Similarity	NPD9268	Approved
0.6951	Remote Similarity	NPD6832	Phase 2
0.695	Remote Similarity	NPD7999	Approved
0.6948	Remote Similarity	NPD8067	Phase 3
0.6946	Remote Similarity	NPD6355	Discontinued
0.6941	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6004	Phase 3
0.6941	Remote Similarity	NPD6005	Phase 3
0.6941	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6002	Phase 3
0.6937	Remote Similarity	NPD1281	Approved
0.6919	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4110	Phase 3
0.6915	Remote Similarity	NPD7584	Approved
0.6907	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6212	Phase 3

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