NPASS Compound

Structure

CID184928 OpenBabel06191715562D 35 37 0 0 1 0 0 0 0 0999 V2000 -3.0548 -3.6251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4260 -5.1433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5573 -4.0833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1175 -4.0833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1890 0.7366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7492 0.7366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5181 1.4075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4911 1.8328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3437 2.2581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0961 2.2581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8651 -2.5360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7815 -1.3417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3417 -1.3417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4256 -3.8396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3021 -4.2027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1943 -3.2068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2455 -3.2068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8651 -1.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4253 -1.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0270 -0.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5872 -0.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1943 -0.9164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2455 -0.9164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4253 -2.5360 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3562 0.2455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9164 0.2455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4398 -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 3.9434 -0.1798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5036 -0.1798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6017 1.1619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1619 1.1619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0981 1.3417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3417 1.3417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3018 -2.8990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 9 33 1 0 0 0 0 10 34 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 19 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 35 1 0 0 0 0 16 3 1 6 0 0 0 16 17 1 0 0 0 0 17 4 1 6 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 21 26 2 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 27 2 0 0 0 0 23 28 2 0 0 0 0 24 35 1 1 0 0 0 25 27 1 0 0 0 0 25 31 1 0 0 0 0 26 28 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.28
Volume:	512.888
LogP:	5.187
LogD:	4.236
LogS:	-5.681
# Rotatable Bonds:	9
TPSA:	64.61
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.432
Synthetic Accessibility Score:	3.817
Fsp3:	0.571
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:	-4.793
MDCK Permeability:	2.7438671168056317e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.193

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	68.27765655517578%
Volume Distribution (VD):	0.944
Pgp-substrate:	12.832697868347168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.569
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.267
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.697
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	4.429
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.439
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.863
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.566
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.07

Download Data

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

Natural Product: NPC184928

Natural Product ID:	NPC184928
*Common Name:**	VLURTMXFQXKLON-WOGXIUBCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VLURTMXFQXKLON-WOGXIUBCSA-N
Standard InCHI:	InChI=1S/C28H40O7/c1-15(2)14-35-24-17(4)16(3)11-18-12-20(29-5)25(31-7)27(33-9)22(18)23-19(24)13-21(30-6)26(32-8)28(23)34-10/h12-13,15-17,24H,11,14H2,1-10H3/t16-,17-,24+/m0/s1
SMILES:	CC(C)CO[C@@H]1[C@@H](C)[C@@H](C)Cc2cc(c(c(c2-c2c1cc(c(c2OC)OC)OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386333
PubChem CID:	71726170
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[483613]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	200000.0	nM	PMID[483613]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[483613]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[483613]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[483613]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5900.0	nM	PMID[483613]
NPT27	Others	Unspecified		Ratio CC50/EC50	>	33.7	n.a.	PMID[483613]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[483613]

☑ 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 NPC184928 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	509
0.1-0.2	1577
0.2-0.3	4426
0.3-0.4	12551
0.4-0.5	5891
0.5-0.6	4439
0.6-0.7	8964
0.7-0.8	3230
0.8-0.85	765
0.85-0.9	293
0.9-0.95	47
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC141493
0.9758	High Similarity	NPC149008
0.9758	High Similarity	NPC207702
0.9758	High Similarity	NPC283114
0.9538	High Similarity	NPC865
0.9466	High Similarity	NPC471183
0.9453	High Similarity	NPC475856
0.9453	High Similarity	NPC102256
0.9313	High Similarity	NPC133025
0.9297	High Similarity	NPC237169
0.9297	High Similarity	NPC470624
0.9286	High Similarity	NPC88297
0.9286	High Similarity	NPC186845
0.9286	High Similarity	NPC9891
0.9242	High Similarity	NPC3072
0.9242	High Similarity	NPC301765
0.9242	High Similarity	NPC156948
0.9242	High Similarity	NPC86605
0.9242	High Similarity	NPC46277
0.9185	High Similarity	NPC469630
0.916	High Similarity	NPC276026
0.916	High Similarity	NPC188378
0.916	High Similarity	NPC469659
0.916	High Similarity	NPC289258
0.916	High Similarity	NPC185680
0.916	High Similarity	NPC256776
0.916	High Similarity	NPC56764
0.916	High Similarity	NPC7515
0.916	High Similarity	NPC145722
0.916	High Similarity	NPC206737
0.916	High Similarity	NPC555
0.9134	High Similarity	NPC112571
0.9134	High Similarity	NPC285725
0.9134	High Similarity	NPC50683
0.9118	High Similarity	NPC326144
0.9091	High Similarity	NPC180602
0.9091	High Similarity	NPC55239
0.9091	High Similarity	NPC240279
0.9091	High Similarity	NPC214853
0.9062	High Similarity	NPC202904
0.9062	High Similarity	NPC8050
0.9062	High Similarity	NPC471986
0.9062	High Similarity	NPC189248
0.9062	High Similarity	NPC473093
0.9062	High Similarity	NPC473092
0.9051	High Similarity	NPC318286
0.9051	High Similarity	NPC327651
0.9044	High Similarity	NPC76415
0.9044	High Similarity	NPC218510
0.904	High Similarity	NPC477886
0.9023	High Similarity	NPC32189
0.8992	High Similarity	NPC54321
0.8992	High Similarity	NPC328682
0.8992	High Similarity	NPC222127
0.8992	High Similarity	NPC31707
0.8992	High Similarity	NPC82862
0.8992	High Similarity	NPC281864
0.8986	High Similarity	NPC321696
0.8986	High Similarity	NPC321958
0.8986	High Similarity	NPC474054
0.8978	High Similarity	NPC87883
0.8971	High Similarity	NPC36531
0.8971	High Similarity	NPC229172
0.8971	High Similarity	NPC230538
0.8971	High Similarity	NPC103637
0.8963	High Similarity	NPC216434
0.8963	High Similarity	NPC103448
0.8921	High Similarity	NPC295297
0.8915	High Similarity	NPC242032
0.8905	High Similarity	NPC324962
0.8889	High Similarity	NPC290714
0.8889	High Similarity	NPC53722
0.8889	High Similarity	NPC201404
0.8872	High Similarity	NPC474478
0.8857	High Similarity	NPC252281
0.8857	High Similarity	NPC198129
0.8857	High Similarity	NPC477375
0.8857	High Similarity	NPC477879
0.8857	High Similarity	NPC327352
0.8841	High Similarity	NPC239254
0.8841	High Similarity	NPC73467
0.8841	High Similarity	NPC121661
0.8841	High Similarity	NPC172171
0.8832	High Similarity	NPC474295
0.8819	High Similarity	NPC261661
0.88	High Similarity	NPC15805
0.88	High Similarity	NPC475961
0.88	High Similarity	NPC254625
0.8794	High Similarity	NPC477376
0.8794	High Similarity	NPC474347
0.8794	High Similarity	NPC322426
0.8794	High Similarity	NPC474393
0.8794	High Similarity	NPC477374
0.8788	High Similarity	NPC149337
0.8788	High Similarity	NPC471983
0.8777	High Similarity	NPC166506
0.8777	High Similarity	NPC197352
0.8777	High Similarity	NPC110763
0.8777	High Similarity	NPC475868
0.8777	High Similarity	NPC189239
0.8741	High Similarity	NPC78047
0.874	High Similarity	NPC312713
0.874	High Similarity	NPC126935
0.874	High Similarity	NPC65933
0.874	High Similarity	NPC172676
0.874	High Similarity	NPC57268
0.874	High Similarity	NPC216929
0.8732	High Similarity	NPC477381
0.8732	High Similarity	NPC470916
0.8732	High Similarity	NPC316989
0.8723	High Similarity	NPC325720
0.8723	High Similarity	NPC316676
0.8722	High Similarity	NPC72046
0.8722	High Similarity	NPC175067
0.8722	High Similarity	NPC261812
0.8722	High Similarity	NPC65183
0.8722	High Similarity	NPC204215
0.8714	High Similarity	NPC252286
0.8714	High Similarity	NPC154971
0.8712	High Similarity	NPC476399
0.8712	High Similarity	NPC224157
0.8712	High Similarity	NPC126836
0.8712	High Similarity	NPC192687
0.8705	High Similarity	NPC18211
0.8696	High Similarity	NPC133934
0.8696	High Similarity	NPC184684
0.8696	High Similarity	NPC184641
0.8696	High Similarity	NPC470917
0.8692	High Similarity	NPC223953
0.8682	High Similarity	NPC18449
0.8682	High Similarity	NPC121783
0.8682	High Similarity	NPC34902
0.8676	High Similarity	NPC196420
0.8676	High Similarity	NPC477938
0.8671	High Similarity	NPC477379
0.8671	High Similarity	NPC224472
0.8667	High Similarity	NPC256262
0.8662	High Similarity	NPC85141
0.8661	High Similarity	NPC472596
0.8657	High Similarity	NPC136750
0.8657	High Similarity	NPC158331
0.8657	High Similarity	NPC263064
0.8657	High Similarity	NPC32778
0.8657	High Similarity	NPC1474
0.8657	High Similarity	NPC266848
0.8652	High Similarity	NPC183083
0.8652	High Similarity	NPC137352
0.8647	High Similarity	NPC474017
0.8636	High Similarity	NPC469951
0.8636	High Similarity	NPC190144
0.8636	High Similarity	NPC469963
0.8626	High Similarity	NPC98745
0.8615	High Similarity	NPC105925
0.8613	High Similarity	NPC230124
0.8613	High Similarity	NPC184613
0.8613	High Similarity	NPC6300
0.8613	High Similarity	NPC471388
0.8613	High Similarity	NPC114171
0.8611	High Similarity	NPC475229
0.8611	High Similarity	NPC477378
0.8611	High Similarity	NPC471154
0.8603	High Similarity	NPC234952
0.8603	High Similarity	NPC471182
0.8603	High Similarity	NPC248727
0.8603	High Similarity	NPC143139
0.8603	High Similarity	NPC205442
0.8603	High Similarity	NPC173660
0.8603	High Similarity	NPC265433
0.8603	High Similarity	NPC162659
0.8603	High Similarity	NPC202846
0.8603	High Similarity	NPC270456
0.8601	High Similarity	NPC473989
0.8593	High Similarity	NPC31530
0.8593	High Similarity	NPC125649
0.8593	High Similarity	NPC209199
0.8593	High Similarity	NPC244983
0.8593	High Similarity	NPC326095
0.8593	High Similarity	NPC287745
0.8582	High Similarity	NPC7744
0.8582	High Similarity	NPC6451
0.8571	High Similarity	NPC469614
0.8571	High Similarity	NPC50250
0.8571	High Similarity	NPC307042
0.8571	High Similarity	NPC473108
0.8571	High Similarity	NPC79184
0.8571	High Similarity	NPC143092
0.8571	High Similarity	NPC469612
0.8561	High Similarity	NPC154866
0.8561	High Similarity	NPC210674
0.856	High Similarity	NPC123948
0.856	High Similarity	NPC81067
0.856	High Similarity	NPC9341
0.8552	High Similarity	NPC308739
0.8552	High Similarity	NPC477377
0.8552	High Similarity	NPC475141
0.8552	High Similarity	NPC297271
0.8552	High Similarity	NPC126405
0.8552	High Similarity	NPC24562
0.8552	High Similarity	NPC16791
0.8552	High Similarity	NPC77237

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 NPC184928 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	431
0.1-0.2	905
0.2-0.3	1932
0.3-0.4	2710
0.4-0.5	1595
0.5-0.6	907
0.6-0.7	560
0.7-0.8	103
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8496	Intermediate Similarity	NPD3027	Phase 3
0.832	Intermediate Similarity	NPD5283	Phase 1
0.8209	Intermediate Similarity	NPD3018	Phase 2
0.8175	Intermediate Similarity	NPD1613	Approved
0.8175	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD3705	Approved
0.8106	Intermediate Similarity	NPD2981	Phase 2
0.8074	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD2983	Phase 2
0.8045	Intermediate Similarity	NPD2982	Phase 2
0.8015	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD4908	Phase 1
0.7862	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD4966	Approved
0.7778	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD4965	Approved
0.777	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD1610	Phase 2
0.7737	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6674	Discontinued
0.7698	Intermediate Similarity	NPD4625	Phase 3
0.7687	Intermediate Similarity	NPD7124	Phase 2
0.7677	Intermediate Similarity	NPD6234	Discontinued
0.7639	Intermediate Similarity	NPD3539	Phase 1
0.7622	Intermediate Similarity	NPD6111	Discontinued
0.7616	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3540	Phase 1
0.7554	Intermediate Similarity	NPD2861	Phase 2
0.7518	Intermediate Similarity	NPD4749	Approved
0.7518	Intermediate Similarity	NPD5109	Approved
0.7518	Intermediate Similarity	NPD5110	Phase 2
0.7518	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5111	Phase 2
0.7516	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4005	Discontinued
0.7483	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3657	Discovery
0.7468	Intermediate Similarity	NPD7199	Phase 2
0.7468	Intermediate Similarity	NPD1934	Approved
0.7463	Intermediate Similarity	NPD1548	Phase 1
0.7453	Intermediate Similarity	NPD7228	Approved
0.7413	Intermediate Similarity	NPD4060	Phase 1
0.7413	Intermediate Similarity	NPD3620	Phase 2
0.7413	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5844	Phase 1
0.7394	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5327	Phase 3
0.7391	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7473	Discontinued
0.7389	Intermediate Similarity	NPD4055	Discovery
0.7388	Intermediate Similarity	NPD5536	Phase 2
0.7375	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3892	Phase 2
0.7315	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6232	Discontinued
0.7308	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2438	Suspended
0.7279	Intermediate Similarity	NPD5691	Approved
0.7273	Intermediate Similarity	NPD7240	Approved
0.7261	Intermediate Similarity	NPD3817	Phase 2
0.7254	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7157	Approved
0.723	Intermediate Similarity	NPD5763	Approved
0.723	Intermediate Similarity	NPD5762	Approved
0.7215	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD8651	Approved
0.72	Intermediate Similarity	NPD7466	Approved
0.7197	Intermediate Similarity	NPD228	Approved
0.7197	Intermediate Similarity	NPD2801	Approved
0.7195	Intermediate Similarity	NPD8156	Discontinued
0.7179	Intermediate Similarity	NPD5089	Approved
0.7179	Intermediate Similarity	NPD5090	Approved
0.7172	Intermediate Similarity	NPD2979	Phase 3
0.7172	Intermediate Similarity	NPD2238	Phase 2
0.7162	Intermediate Similarity	NPD2796	Approved
0.7162	Intermediate Similarity	NPD6099	Approved
0.7162	Intermediate Similarity	NPD6100	Approved
0.7161	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1651	Approved
0.7152	Intermediate Similarity	NPD2677	Approved
0.7143	Intermediate Similarity	NPD7843	Approved
0.7143	Intermediate Similarity	NPD6895	Approved
0.7143	Intermediate Similarity	NPD6896	Approved
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8099	Discontinued
0.7134	Intermediate Similarity	NPD8251	Approved
0.7134	Intermediate Similarity	NPD8252	Approved
0.7133	Intermediate Similarity	NPD5177	Phase 3
0.7123	Intermediate Similarity	NPD5735	Approved
0.7123	Intermediate Similarity	NPD6355	Discontinued
0.7122	Intermediate Similarity	NPD1611	Approved
0.7117	Intermediate Similarity	NPD6166	Phase 2
0.7117	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4678	Approved
0.7115	Intermediate Similarity	NPD4675	Approved
0.7114	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3882	Suspended
0.7099	Intermediate Similarity	NPD2684	Approved
0.7099	Intermediate Similarity	NPD7229	Phase 3
0.7097	Intermediate Similarity	NPD1653	Approved
0.7095	Intermediate Similarity	NPD3748	Approved
0.7092	Intermediate Similarity	NPD2922	Phase 1
0.7089	Intermediate Similarity	NPD7819	Suspended
0.7089	Intermediate Similarity	NPD4585	Approved
0.7089	Intermediate Similarity	NPD1465	Phase 2
0.7078	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3926	Phase 2
0.7048	Intermediate Similarity	NPD7074	Phase 3
0.7045	Intermediate Similarity	NPD3021	Approved
0.7045	Intermediate Similarity	NPD4750	Phase 3
0.7045	Intermediate Similarity	NPD3022	Approved
0.7044	Intermediate Similarity	NPD5353	Approved
0.7029	Intermediate Similarity	NPD3445	Approved
0.7029	Intermediate Similarity	NPD3443	Approved
0.7029	Intermediate Similarity	NPD3444	Approved
0.7021	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4237	Approved
0.702	Intermediate Similarity	NPD4236	Phase 3
0.7	Intermediate Similarity	NPD1091	Approved
0.7	Intermediate Similarity	NPD1375	Discontinued
0.7	Intermediate Similarity	NPD1281	Approved
0.6988	Remote Similarity	NPD7054	Approved
0.6985	Remote Similarity	NPD709	Approved
0.6985	Remote Similarity	NPD6671	Approved
0.698	Remote Similarity	NPD4108	Discontinued
0.6978	Remote Similarity	NPD4626	Approved
0.6974	Remote Similarity	NPD6331	Phase 2
0.6974	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4110	Phase 3
0.6972	Remote Similarity	NPD6696	Suspended
0.697	Remote Similarity	NPD3489	Phase 3
0.6954	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5242	Approved
0.6948	Remote Similarity	NPD4357	Discontinued
0.6948	Remote Similarity	NPD1511	Approved
0.6946	Remote Similarity	NPD7472	Approved
0.6937	Remote Similarity	NPD2563	Approved
0.6937	Remote Similarity	NPD2560	Approved
0.6933	Remote Similarity	NPD6959	Discontinued
0.6933	Remote Similarity	NPD1247	Approved
0.6928	Remote Similarity	NPD3818	Discontinued
0.6928	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2219	Phase 1
0.6923	Remote Similarity	NPD7549	Discontinued
0.6918	Remote Similarity	NPD5718	Phase 2
0.6918	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5451	Approved
0.6914	Remote Similarity	NPD919	Approved
0.6913	Remote Similarity	NPD4536	Approved
0.6913	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4538	Approved
0.6908	Remote Similarity	NPD1652	Phase 2
0.6908	Remote Similarity	NPD3060	Approved
0.6906	Remote Similarity	NPD1357	Approved
0.6906	Remote Similarity	NPD5585	Approved
0.6903	Remote Similarity	NPD4584	Approved
0.6903	Remote Similarity	NPD7447	Phase 1
0.6901	Remote Similarity	NPD1669	Approved
0.6899	Remote Similarity	NPD4380	Phase 2
0.6894	Remote Similarity	NPD6788	Approved
0.6894	Remote Similarity	NPD290	Approved
0.6892	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5124	Phase 1
0.689	Remote Similarity	NPD3787	Discontinued
0.6889	Remote Similarity	NPD5535	Approved
0.6887	Remote Similarity	NPD7266	Discontinued
0.6879	Remote Similarity	NPD422	Phase 1
0.6875	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2154	Approved
0.6867	Remote Similarity	NPD2156	Approved
0.6867	Remote Similarity	NPD2155	Approved
0.6863	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3750	Approved
0.6861	Remote Similarity	NPD6387	Discontinued
0.6859	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD52	Approved
0.6859	Remote Similarity	NPD7526	Approved
0.6859	Remote Similarity	NPD1512	Approved
0.6857	Remote Similarity	NPD17	Approved
0.6855	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1283	Approved
0.6849	Remote Similarity	NPD7095	Approved
0.6849	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4097	Suspended
0.6846	Remote Similarity	NPD6353	Approved
0.6842	Remote Similarity	NPD2808	Discontinued
0.6842	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8054	Approved
0.6842	Remote Similarity	NPD8053	Approved
0.6839	Remote Similarity	NPD7040	Clinical (unspecified phase)

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