NPASS Compound

Structure

NPC471181 OpenBabel07101718202D 32 35 0 0 1 0 0 0 0 0999 V2000 2.4888 3.6153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3079 4.7961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3073 -0.5305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8378 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4189 -0.8192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6148 2.3073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4881 3.7262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7630 2.7803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6148 3.2533 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9459 3.9221 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9459 1.6384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6689 3.2533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3073 3.2533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6689 2.3073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4189 0.8192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.9221 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9459 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3073 2.3073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4881 1.8343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4730 0.8192 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 2.3649 0.8192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3620 4.7961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4189 -0.8192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8378 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8378 1.6384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4881 -0.0576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3649 0.8192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4730 -0.8192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2070 3.5456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2070 2.0150 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 9 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 31 1 0 0 0 0 8 32 1 0 0 0 0 9 1 1 6 0 0 0 9 10 1 0 0 0 0 10 2 1 6 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 19 2 0 0 0 0 13 31 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 20 2 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 6 0 0 0 18 22 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 32 1 0 0 0 0 20 28 1 0 0 0 0 21 22 2 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.16
Volume:	432.795
LogP:	3.772
LogD:	1.807
LogS:	-2.983
# Rotatable Bonds:	4
TPSA:	123.91
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.648
Synthetic Accessibility Score:	4.028
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.524
MDCK Permeability:	7.736458428553306e-06
Pgp-inhibitor:	0.222
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	93.03654479980469%
Volume Distribution (VD):	0.69
Pgp-substrate:	6.915444850921631%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.357
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.216
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	2.088
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.213
Human Hepatotoxicity (H-HT):	0.401
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.403
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.032
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.598

Download Data

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

Natural Product: NPC471181

Natural Product ID:	NPC471181
*Common Name:**	CYOQLUBFWYSAMW-VHCOLVSPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CYOQLUBFWYSAMW-VHCOLVSPSA-N
Standard InCHI:	InChI=1S/C23H26O9/c1-9-6-11-14(21(29-4)22(30-5)18(25)16(11)23(26)27)15-12(17(24)10(9)2)7-13-19(20(15)28-3)32-8-31-13/h7,9-10,17,24-25H,6,8H2,1-5H3,(H,26,27)/t9-,10-,17-/m1/s1
SMILES:	CC1CC2=C(C3=C(C4=C(C=C3C(C1C)O)OCO4)OC)C(=C(C(=C2C(=O)O)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386330
PubChem CID:	71726087
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[558917]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	75200.0	nM	PMID[558917]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	9200.0	nM	PMID[558917]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5900.0	nM	PMID[558917]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[558917]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	1400.0	nM	PMID[558917]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	55.3	n.a.	PMID[558917]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[558917]

☑ 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 NPC471181 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	375
0.1-0.2	1570
0.2-0.3	3521
0.3-0.4	8143
0.4-0.5	10103
0.5-0.6	4028
0.6-0.7	5098
0.7-0.8	7062
0.8-0.85	2348
0.85-0.9	424
0.9-0.95	23
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9812	High Similarity	NPC471180
0.9383	High Similarity	NPC469475
0.9383	High Similarity	NPC469518
0.9277	High Similarity	NPC178737
0.9277	High Similarity	NPC469506
0.9146	High Similarity	NPC475865
0.9096	High Similarity	NPC311912
0.9085	High Similarity	NPC469512
0.908	High Similarity	NPC474770
0.9074	High Similarity	NPC190020
0.9074	High Similarity	NPC77679
0.9074	High Similarity	NPC84935
0.9042	High Similarity	NPC88557
0.9018	High Similarity	NPC325122
0.9012	High Similarity	NPC150227
0.8951	High Similarity	NPC199926
0.8951	High Similarity	NPC82592
0.8951	High Similarity	NPC238834
0.8951	High Similarity	NPC16082
0.8951	High Similarity	NPC79998
0.8929	High Similarity	NPC117911
0.8922	High Similarity	NPC472452
0.8909	High Similarity	NPC473106
0.8909	High Similarity	NPC103201
0.8896	High Similarity	NPC469474
0.8889	High Similarity	NPC281477
0.8889	High Similarity	NPC196771
0.8882	High Similarity	NPC477881
0.8862	High Similarity	NPC475738
0.8855	High Similarity	NPC474763
0.8855	High Similarity	NPC61141
0.8855	High Similarity	NPC144843
0.8855	High Similarity	NPC76687
0.8848	High Similarity	NPC292415
0.8848	High Similarity	NPC470358
0.8844	High Similarity	NPC170203
0.8834	High Similarity	NPC476065
0.8827	High Similarity	NPC474514
0.8827	High Similarity	NPC474606
0.882	High Similarity	NPC475756
0.882	High Similarity	NPC96501
0.881	High Similarity	NPC474042
0.881	High Similarity	NPC320471
0.881	High Similarity	NPC329119
0.881	High Similarity	NPC174734
0.881	High Similarity	NPC118162
0.881	High Similarity	NPC83049
0.8795	High Similarity	NPC474779
0.8795	High Similarity	NPC349525
0.8788	High Similarity	NPC315157
0.8788	High Similarity	NPC45846
0.8786	High Similarity	NPC212290
0.878	High Similarity	NPC227062
0.878	High Similarity	NPC477380
0.878	High Similarity	NPC301897
0.878	High Similarity	NPC54928
0.8779	High Similarity	NPC473713
0.8773	High Similarity	NPC287504
0.8773	High Similarity	NPC136757
0.8765	High Similarity	NPC477883
0.8765	High Similarity	NPC200773
0.8765	High Similarity	NPC471154
0.8765	High Similarity	NPC272566
0.8765	High Similarity	NPC220577
0.8765	High Similarity	NPC240768
0.8765	High Similarity	NPC212748
0.8765	High Similarity	NPC17219
0.8757	High Similarity	NPC116745
0.8757	High Similarity	NPC298847
0.8757	High Similarity	NPC477502
0.8757	High Similarity	NPC79322
0.875	High Similarity	NPC326520
0.875	High Similarity	NPC327652
0.8743	High Similarity	NPC215612
0.8743	High Similarity	NPC125991
0.8743	High Similarity	NPC22324
0.8736	High Similarity	NPC208797
0.8736	High Similarity	NPC53680
0.8735	High Similarity	NPC24627
0.8735	High Similarity	NPC150943
0.8735	High Similarity	NPC200594
0.8735	High Similarity	NPC472055
0.8735	High Similarity	NPC268718
0.8735	High Similarity	NPC91634
0.8735	High Similarity	NPC47623
0.8728	High Similarity	NPC477882
0.8728	High Similarity	NPC477880
0.8727	High Similarity	NPC477885
0.8727	High Similarity	NPC475592
0.8721	High Similarity	NPC470454
0.8721	High Similarity	NPC472607
0.8721	High Similarity	NPC199533
0.8713	High Similarity	NPC260263
0.8712	High Similarity	NPC245948
0.8712	High Similarity	NPC24562
0.8704	High Similarity	NPC234152
0.8704	High Similarity	NPC179178
0.8698	High Similarity	NPC13481
0.8698	High Similarity	NPC170245
0.8698	High Similarity	NPC207575
0.8698	High Similarity	NPC178851
0.869	High Similarity	NPC317781
0.8688	High Similarity	NPC138978
0.8683	High Similarity	NPC295009
0.8683	High Similarity	NPC87431
0.8683	High Similarity	NPC260640
0.8678	High Similarity	NPC240887
0.8678	High Similarity	NPC470091
0.8678	High Similarity	NPC329161
0.8675	High Similarity	NPC279732
0.8675	High Similarity	NPC470339
0.8671	High Similarity	NPC472723
0.8671	High Similarity	NPC79736
0.8671	High Similarity	NPC67629
0.8663	High Similarity	NPC46640
0.8663	High Similarity	NPC263119
0.8663	High Similarity	NPC98776
0.8663	High Similarity	NPC219600
0.8663	High Similarity	NPC166674
0.8663	High Similarity	NPC34436
0.8659	High Similarity	NPC312763
0.8659	High Similarity	NPC178195
0.8659	High Similarity	NPC348849
0.8659	High Similarity	NPC25127
0.8655	High Similarity	NPC298778
0.8655	High Similarity	NPC477572
0.8655	High Similarity	NPC477571
0.8655	High Similarity	NPC477573
0.865	High Similarity	NPC104353
0.865	High Similarity	NPC215921
0.865	High Similarity	NPC204350
0.865	High Similarity	NPC70016
0.865	High Similarity	NPC477699
0.8647	High Similarity	NPC473094
0.8644	High Similarity	NPC475360
0.8644	High Similarity	NPC105591
0.8639	High Similarity	NPC477884
0.8639	High Similarity	NPC165720
0.8639	High Similarity	NPC7752
0.8639	High Similarity	NPC471788
0.8634	High Similarity	NPC316676
0.8634	High Similarity	NPC304821
0.8634	High Similarity	NPC325720
0.8631	High Similarity	NPC127782
0.8631	High Similarity	NPC42797
0.8631	High Similarity	NPC472635
0.8631	High Similarity	NPC473445
0.8631	High Similarity	NPC300537
0.8631	High Similarity	NPC469575
0.8623	High Similarity	NPC155302
0.8623	High Similarity	NPC36217
0.8623	High Similarity	NPC225624
0.8623	High Similarity	NPC161947
0.8623	High Similarity	NPC285973
0.8621	High Similarity	NPC469600
0.8621	High Similarity	NPC267549
0.8614	High Similarity	NPC163527
0.8614	High Similarity	NPC167595
0.8614	High Similarity	NPC115281
0.8614	High Similarity	NPC181168
0.8614	High Similarity	NPC19947
0.8614	High Similarity	NPC472860
0.8614	High Similarity	NPC207584
0.8614	High Similarity	NPC179732
0.8614	High Similarity	NPC78103
0.8613	High Similarity	NPC68381
0.8613	High Similarity	NPC108202
0.8613	High Similarity	NPC146803
0.8613	High Similarity	NPC63105
0.8613	High Similarity	NPC474345
0.8613	High Similarity	NPC469354
0.8606	High Similarity	NPC38898
0.8606	High Similarity	NPC16286
0.8605	High Similarity	NPC211594
0.8605	High Similarity	NPC38438
0.8605	High Similarity	NPC235575
0.8605	High Similarity	NPC261254
0.8605	High Similarity	NPC223375
0.8605	High Similarity	NPC472386
0.8605	High Similarity	NPC254540
0.8605	High Similarity	NPC172807
0.8605	High Similarity	NPC475825
0.8605	High Similarity	NPC256760
0.8603	High Similarity	NPC264302
0.8598	High Similarity	NPC126405
0.8598	High Similarity	NPC297271
0.8598	High Similarity	NPC199773
0.8598	High Similarity	NPC178574
0.8598	High Similarity	NPC53669
0.8598	High Similarity	NPC65591
0.8598	High Similarity	NPC16791
0.8598	High Similarity	NPC217708
0.8598	High Similarity	NPC77237
0.8598	High Similarity	NPC295646
0.8598	High Similarity	NPC308739
0.8596	High Similarity	NPC229687
0.8596	High Similarity	NPC473095
0.8596	High Similarity	NPC473096
0.8596	High Similarity	NPC476771
0.8596	High Similarity	NPC259905

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 NPC471181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	932
0.2-0.3	1942
0.3-0.4	2631
0.4-0.5	1807
0.5-0.6	940
0.6-0.7	401
0.7-0.8	137
0.8-0.85	31
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8757	High Similarity	NPD3818	Discontinued
0.8743	High Similarity	NPD6232	Discontinued
0.8712	High Similarity	NPD37	Approved
0.8698	High Similarity	NPD7473	Discontinued
0.8675	High Similarity	NPD6234	Discontinued
0.8554	High Similarity	NPD4966	Approved
0.8554	High Similarity	NPD4965	Approved
0.8554	High Similarity	NPD4967	Phase 2
0.8439	Intermediate Similarity	NPD7074	Phase 3
0.843	Intermediate Similarity	NPD7228	Approved
0.84	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD7054	Approved
0.8333	Intermediate Similarity	NPD7472	Approved
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD2533	Approved
0.8282	Intermediate Similarity	NPD2534	Approved
0.8282	Intermediate Similarity	NPD2532	Approved
0.8263	Intermediate Similarity	NPD1934	Approved
0.8246	Intermediate Similarity	NPD7199	Phase 2
0.8239	Intermediate Similarity	NPD6559	Discontinued
0.8225	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD3882	Suspended
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.8171	Intermediate Similarity	NPD5844	Phase 1
0.8136	Intermediate Similarity	NPD7251	Discontinued
0.8122	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD2801	Approved
0.8107	Intermediate Similarity	NPD1465	Phase 2
0.8103	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD6166	Phase 2
0.809	Intermediate Similarity	NPD7808	Phase 3
0.8081	Intermediate Similarity	NPD5494	Approved
0.8072	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD3817	Phase 2
0.8046	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD4380	Phase 2
0.8025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7819	Suspended
0.7966	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7075	Discontinued
0.7956	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7240	Approved
0.7836	Intermediate Similarity	NPD6801	Discontinued
0.7833	Intermediate Similarity	NPD7685	Pre-registration
0.7829	Intermediate Similarity	NPD6959	Discontinued
0.7791	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8151	Discontinued
0.7784	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD1511	Approved
0.7778	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD8312	Approved
0.7747	Intermediate Similarity	NPD8313	Approved
0.7714	Intermediate Similarity	NPD919	Approved
0.7692	Intermediate Similarity	NPD1512	Approved
0.7684	Intermediate Similarity	NPD5710	Approved
0.7684	Intermediate Similarity	NPD5711	Approved
0.7683	Intermediate Similarity	NPD2935	Discontinued
0.7654	Intermediate Similarity	NPD230	Phase 1
0.7644	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6799	Approved
0.7572	Intermediate Similarity	NPD7411	Suspended
0.7557	Intermediate Similarity	NPD3749	Approved
0.7543	Intermediate Similarity	NPD5402	Approved
0.7542	Intermediate Similarity	NPD3926	Phase 2
0.7529	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD1247	Approved
0.7527	Intermediate Similarity	NPD8434	Phase 2
0.7526	Intermediate Similarity	NPD7435	Discontinued
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7515	Intermediate Similarity	NPD1510	Phase 2
0.7514	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD943	Approved
0.7485	Intermediate Similarity	NPD1240	Approved
0.7461	Intermediate Similarity	NPD6781	Approved
0.7461	Intermediate Similarity	NPD6779	Approved
0.7461	Intermediate Similarity	NPD6777	Approved
0.7461	Intermediate Similarity	NPD6780	Approved
0.7461	Intermediate Similarity	NPD6776	Approved
0.7461	Intermediate Similarity	NPD6782	Approved
0.7461	Intermediate Similarity	NPD6778	Approved
0.7442	Intermediate Similarity	NPD920	Approved
0.744	Intermediate Similarity	NPD2800	Approved
0.7437	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7783	Phase 2
0.7436	Intermediate Similarity	NPD7680	Approved
0.7425	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3751	Discontinued
0.7413	Intermediate Similarity	NPD7930	Approved
0.7396	Intermediate Similarity	NPD4628	Phase 3
0.7394	Intermediate Similarity	NPD1607	Approved
0.7389	Intermediate Similarity	NPD7229	Phase 3
0.7389	Intermediate Similarity	NPD3787	Discontinued
0.7381	Intermediate Similarity	NPD1549	Phase 2
0.7368	Intermediate Similarity	NPD7390	Discontinued
0.7356	Intermediate Similarity	NPD7458	Discontinued
0.7356	Intermediate Similarity	NPD3226	Approved
0.7353	Intermediate Similarity	NPD6190	Approved
0.7341	Intermediate Similarity	NPD5403	Approved
0.734	Intermediate Similarity	NPD8150	Discontinued
0.7337	Intermediate Similarity	NPD1243	Approved
0.7326	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7874	Approved
0.7296	Intermediate Similarity	NPD5006	Approved
0.7296	Intermediate Similarity	NPD5005	Approved
0.7294	Intermediate Similarity	NPD3750	Approved
0.7289	Intermediate Similarity	NPD6651	Approved
0.7288	Intermediate Similarity	NPD8455	Phase 2
0.7262	Intermediate Similarity	NPD2796	Approved
0.7259	Intermediate Similarity	NPD7698	Approved
0.7259	Intermediate Similarity	NPD7696	Phase 3
0.7259	Intermediate Similarity	NPD7697	Approved
0.7229	Intermediate Similarity	NPD447	Suspended
0.7225	Intermediate Similarity	NPD5401	Approved
0.7222	Intermediate Similarity	NPD8319	Approved
0.7222	Intermediate Similarity	NPD7870	Phase 2
0.7222	Intermediate Similarity	NPD7871	Phase 2
0.7222	Intermediate Similarity	NPD8320	Phase 1
0.7219	Intermediate Similarity	NPD7266	Discontinued
0.7209	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6823	Phase 2
0.7204	Intermediate Similarity	NPD5953	Discontinued
0.7202	Intermediate Similarity	NPD6534	Approved
0.7202	Intermediate Similarity	NPD6535	Approved
0.7202	Intermediate Similarity	NPD2799	Discontinued
0.72	Intermediate Similarity	NPD7701	Phase 2
0.7194	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4420	Approved
0.7178	Intermediate Similarity	NPD7801	Approved
0.7169	Intermediate Similarity	NPD1613	Approved
0.7169	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1551	Phase 2
0.7159	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5242	Approved
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5353	Approved
0.7135	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6674	Discontinued
0.7128	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1933	Approved
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2346	Discontinued
0.7097	Intermediate Similarity	NPD7286	Phase 2
0.7092	Intermediate Similarity	NPD7699	Phase 2
0.7092	Intermediate Similarity	NPD7700	Phase 2
0.7081	Intermediate Similarity	NPD9269	Phase 2
0.7073	Intermediate Similarity	NPD9494	Approved
0.7066	Intermediate Similarity	NPD4060	Phase 1
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD2438	Suspended
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD5405	Approved
0.7049	Intermediate Similarity	NPD8127	Discontinued
0.7048	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3705	Approved
0.7018	Intermediate Similarity	NPD2344	Approved
0.7	Intermediate Similarity	NPD3748	Approved
0.6994	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1283	Approved
0.6994	Remote Similarity	NPD7003	Approved
0.698	Remote Similarity	NPD7584	Approved
0.6974	Remote Similarity	NPD6213	Phase 3
0.6974	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6212	Phase 3
0.697	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3764	Approved
0.6931	Remote Similarity	NPD7999	Approved
0.693	Remote Similarity	NPD8067	Phase 3
0.6928	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7028	Phase 2
0.6923	Remote Similarity	NPD6355	Discontinued
0.6919	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2798	Approved
0.6901	Remote Similarity	NPD7033	Discontinued
0.6893	Remote Similarity	NPD6273	Approved
0.6889	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6385	Approved
0.6889	Remote Similarity	NPD6386	Approved
0.6864	Remote Similarity	NPD2979	Phase 3
0.6864	Remote Similarity	NPD3620	Phase 2
0.6864	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7585	Approved
0.686	Remote Similarity	NPD6099	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