NPASS Compound

Structure

NPC156539 OpenBabel07101718302D 25 27 0 0 0 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 8 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 13 18 2 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 23 2 0 0 0 0 17 24 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.06
Volume:	329.382
LogP:	2.293
LogD:	1.228
LogS:	-3.498
# Rotatable Bonds:	2
TPSA:	135.29
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	2.639
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.704
MDCK Permeability:	6.340792879200308e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.045
30% Bioavailability (F30%):	0.5

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	97.41197967529297%
Volume Distribution (VD):	0.36
Pgp-substrate:	2.3918497562408447%

ADMET: Metabolism

CYP1A2-inhibitor:	0.649
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.591
CYP2C9-substrate:	0.209
CYP2D6-inhibitor:	0.435
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.065

ADMET: Excretion

Clearance (CL):	0.857
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.916
Drug-inuced Liver Injury (DILI):	0.992
AMES Toxicity:	0.602
Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.686
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.663

Download Data

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

Natural Product: NPC156539

Natural Product ID:	NPC156539
*Common Name:**	OZTXUNBXAHGFHP-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OZTXUNBXAHGFHP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O7/c19-10-6-9(7-11(20)14(10)21)13-17(24)15(22)12(16(23)18(13)25)8-4-2-1-3-5-8/h1-7,19-22,25H
SMILES:	OC1=C(c2cc(O)c(c(c2)O)O)C(=O)C(=C(C1=O)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470336
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001310] Benzenetriols and derivatives [CHEMONTID:0000397] Pyrogallols and derivatives

*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
NPO33054	stilbella sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[15787429]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	=	3900.0	nM	PMID[533948]

☑ 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 NPC156539 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	366
0.1-0.2	1652
0.2-0.3	4514
0.3-0.4	12226
0.4-0.5	6028
0.5-0.6	5271
0.6-0.7	8024
0.7-0.8	4446
0.8-0.85	145
0.85-0.9	21
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9417	High Similarity	NPC294361
0.9417	High Similarity	NPC236520
0.92	High Similarity	NPC107672
0.8984	High Similarity	NPC233056
0.8984	High Similarity	NPC26697
0.8915	High Similarity	NPC34070
0.8915	High Similarity	NPC469526
0.8846	High Similarity	NPC135801
0.8837	High Similarity	NPC244441
0.879	High Similarity	NPC248363
0.8731	High Similarity	NPC175552
0.8722	High Similarity	NPC194764
0.8722	High Similarity	NPC264112
0.8722	High Similarity	NPC65005
0.8712	High Similarity	NPC248150
0.8689	High Similarity	NPC299252
0.8689	High Similarity	NPC277394
0.8689	High Similarity	NPC61062
0.8657	High Similarity	NPC290030
0.8657	High Similarity	NPC170742
0.8529	High Similarity	NPC472903
0.8519	High Similarity	NPC476393
0.8516	High Similarity	NPC13238
0.85	High Similarity	NPC21162
0.848	Intermediate Similarity	NPC158222
0.8467	Intermediate Similarity	NPC203063
0.8455	Intermediate Similarity	NPC4665
0.843	Intermediate Similarity	NPC268032
0.8413	Intermediate Similarity	NPC159525
0.8406	Intermediate Similarity	NPC110419
0.8406	Intermediate Similarity	NPC472904
0.8385	Intermediate Similarity	NPC8745
0.8372	Intermediate Similarity	NPC85565
0.837	Intermediate Similarity	NPC129752
0.8369	Intermediate Similarity	NPC20791
0.8369	Intermediate Similarity	NPC179271
0.8359	Intermediate Similarity	NPC225710
0.8358	Intermediate Similarity	NPC4170
0.8345	Intermediate Similarity	NPC284556
0.8345	Intermediate Similarity	NPC301178
0.8345	Intermediate Similarity	NPC312256
0.8333	Intermediate Similarity	NPC58427
0.8333	Intermediate Similarity	NPC114392
0.8333	Intermediate Similarity	NPC105727
0.8333	Intermediate Similarity	NPC34864
0.8322	Intermediate Similarity	NPC87125
0.8322	Intermediate Similarity	NPC270465
0.8321	Intermediate Similarity	NPC324209
0.832	Intermediate Similarity	NPC150919
0.831	Intermediate Similarity	NPC51443
0.831	Intermediate Similarity	NPC74881
0.8309	Intermediate Similarity	NPC223836
0.8308	Intermediate Similarity	NPC10926
0.8286	Intermediate Similarity	NPC471417
0.8286	Intermediate Similarity	NPC254659
0.8286	Intermediate Similarity	NPC238629
0.8281	Intermediate Similarity	NPC115159
0.8281	Intermediate Similarity	NPC143427
0.8281	Intermediate Similarity	NPC267552
0.8281	Intermediate Similarity	NPC73532
0.8281	Intermediate Similarity	NPC242895
0.8281	Intermediate Similarity	NPC224273
0.8281	Intermediate Similarity	NPC45438
0.8281	Intermediate Similarity	NPC19174
0.8279	Intermediate Similarity	NPC297657
0.8264	Intermediate Similarity	NPC188871
0.8264	Intermediate Similarity	NPC286342
0.8264	Intermediate Similarity	NPC149127
0.8258	Intermediate Similarity	NPC234175
0.8258	Intermediate Similarity	NPC79332
0.825	Intermediate Similarity	NPC176527
0.8239	Intermediate Similarity	NPC169749
0.8227	Intermediate Similarity	NPC242893
0.8227	Intermediate Similarity	NPC105213
0.8227	Intermediate Similarity	NPC38065
0.8227	Intermediate Similarity	NPC207732
0.8227	Intermediate Similarity	NPC142165
0.8227	Intermediate Similarity	NPC279121
0.8217	Intermediate Similarity	NPC133909
0.8217	Intermediate Similarity	NPC32032
0.8217	Intermediate Similarity	NPC86900
0.8214	Intermediate Similarity	NPC291078
0.8211	Intermediate Similarity	NPC51698
0.8207	Intermediate Similarity	NPC252933
0.8207	Intermediate Similarity	NPC200740
0.8207	Intermediate Similarity	NPC260895
0.8207	Intermediate Similarity	NPC54394
0.8207	Intermediate Similarity	NPC125062
0.8203	Intermediate Similarity	NPC297186
0.8195	Intermediate Similarity	NPC92624
0.8194	Intermediate Similarity	NPC195351
0.8182	Intermediate Similarity	NPC95864
0.8182	Intermediate Similarity	NPC140840
0.8182	Intermediate Similarity	NPC108406
0.8182	Intermediate Similarity	NPC86847
0.8169	Intermediate Similarity	NPC70136
0.8169	Intermediate Similarity	NPC157133
0.8156	Intermediate Similarity	NPC175013
0.8156	Intermediate Similarity	NPC287722
0.8151	Intermediate Similarity	NPC55205
0.8151	Intermediate Similarity	NPC63187
0.8151	Intermediate Similarity	NPC82325
0.8151	Intermediate Similarity	NPC279989
0.8151	Intermediate Similarity	NPC157784
0.8151	Intermediate Similarity	NPC37684
0.8148	Intermediate Similarity	NPC175738
0.8145	Intermediate Similarity	NPC62546
0.8145	Intermediate Similarity	NPC162113
0.814	Intermediate Similarity	NPC472271
0.814	Intermediate Similarity	NPC472892
0.814	Intermediate Similarity	NPC196976
0.814	Intermediate Similarity	NPC156139
0.8138	Intermediate Similarity	NPC77858
0.8134	Intermediate Similarity	NPC259942
0.8125	Intermediate Similarity	NPC203747
0.8125	Intermediate Similarity	NPC19545
0.8125	Intermediate Similarity	NPC194653
0.8125	Intermediate Similarity	NPC265454
0.8125	Intermediate Similarity	NPC139364
0.8125	Intermediate Similarity	NPC119059
0.8125	Intermediate Similarity	NPC80710
0.8125	Intermediate Similarity	NPC254702
0.8125	Intermediate Similarity	NPC42464
0.8125	Intermediate Similarity	NPC3036
0.8125	Intermediate Similarity	NPC34634
0.812	Intermediate Similarity	NPC179898
0.812	Intermediate Similarity	NPC24869
0.8116	Intermediate Similarity	NPC264022
0.8112	Intermediate Similarity	NPC165389
0.811	Intermediate Similarity	NPC144343
0.811	Intermediate Similarity	NPC63126
0.8106	Intermediate Similarity	NPC267846
0.8102	Intermediate Similarity	NPC208760
0.8099	Intermediate Similarity	NPC257025
0.8095	Intermediate Similarity	NPC125487
0.8095	Intermediate Similarity	NPC236223
0.8095	Intermediate Similarity	NPC281703
0.8095	Intermediate Similarity	NPC141212
0.8095	Intermediate Similarity	NPC179126
0.8095	Intermediate Similarity	NPC270620
0.8095	Intermediate Similarity	NPC78326
0.8092	Intermediate Similarity	NPC288945
0.8088	Intermediate Similarity	NPC471749
0.8082	Intermediate Similarity	NPC133953
0.8082	Intermediate Similarity	NPC225731
0.8082	Intermediate Similarity	NPC59162
0.8082	Intermediate Similarity	NPC304295
0.8082	Intermediate Similarity	NPC28274
0.8082	Intermediate Similarity	NPC205046
0.8082	Intermediate Similarity	NPC50403
0.8074	Intermediate Similarity	NPC264145
0.8074	Intermediate Similarity	NPC198388
0.8069	Intermediate Similarity	NPC69430
0.8069	Intermediate Similarity	NPC40290
0.8069	Intermediate Similarity	NPC264550
0.8069	Intermediate Similarity	NPC139293
0.8069	Intermediate Similarity	NPC159103
0.8069	Intermediate Similarity	NPC195763
0.8069	Intermediate Similarity	NPC264289
0.8069	Intermediate Similarity	NPC52005
0.8069	Intermediate Similarity	NPC137062
0.8069	Intermediate Similarity	NPC223579
0.8069	Intermediate Similarity	NPC142876
0.8069	Intermediate Similarity	NPC333691
0.8069	Intermediate Similarity	NPC287101
0.8069	Intermediate Similarity	NPC306343
0.8069	Intermediate Similarity	NPC105512
0.8069	Intermediate Similarity	NPC38545
0.8069	Intermediate Similarity	NPC171916
0.8069	Intermediate Similarity	NPC183950
0.8069	Intermediate Similarity	NPC200060
0.8062	Intermediate Similarity	NPC98305
0.806	Intermediate Similarity	NPC474998
0.806	Intermediate Similarity	NPC109123
0.806	Intermediate Similarity	NPC102829
0.806	Intermediate Similarity	NPC120488
0.806	Intermediate Similarity	NPC94810
0.8058	Intermediate Similarity	NPC230811
0.8056	Intermediate Similarity	NPC125449
0.8056	Intermediate Similarity	NPC77598
0.8056	Intermediate Similarity	NPC130230
0.8056	Intermediate Similarity	NPC168803
0.8056	Intermediate Similarity	NPC188074
0.8056	Intermediate Similarity	NPC239312
0.8056	Intermediate Similarity	NPC43123
0.8056	Intermediate Similarity	NPC275772
0.8049	Intermediate Similarity	NPC222084
0.8047	Intermediate Similarity	NPC217174
0.8047	Intermediate Similarity	NPC156654
0.8045	Intermediate Similarity	NPC100067
0.8045	Intermediate Similarity	NPC30501
0.8045	Intermediate Similarity	NPC169250
0.8045	Intermediate Similarity	NPC23126
0.8045	Intermediate Similarity	NPC162612
0.8045	Intermediate Similarity	NPC105157
0.8045	Intermediate Similarity	NPC266689
0.8045	Intermediate Similarity	NPC98254
0.8045	Intermediate Similarity	NPC214620
0.8045	Intermediate Similarity	NPC190043
0.8045	Intermediate Similarity	NPC103356

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 NPC156539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	952
0.2-0.3	1524
0.3-0.4	2997
0.4-0.5	1889
0.5-0.6	1056
0.6-0.7	320
0.7-0.8	60
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8846	High Similarity	NPD943	Approved
0.8444	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD1512	Approved
0.8359	Intermediate Similarity	NPD9269	Phase 2
0.8227	Intermediate Similarity	NPD1511	Approved
0.8047	Intermediate Similarity	NPD9268	Approved
0.7958	Intermediate Similarity	NPD6190	Approved
0.7956	Intermediate Similarity	NPD230	Phase 1
0.7905	Intermediate Similarity	NPD1934	Approved
0.7867	Intermediate Similarity	NPD3882	Suspended
0.7852	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD2801	Approved
0.7786	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1242	Phase 1
0.768	Intermediate Similarity	NPD3021	Approved
0.768	Intermediate Similarity	NPD3022	Approved
0.766	Intermediate Similarity	NPD1510	Phase 2
0.7628	Intermediate Similarity	NPD6166	Phase 2
0.7628	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3817	Phase 2
0.7551	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1240	Approved
0.7483	Intermediate Similarity	NPD7390	Discontinued
0.7481	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1201	Approved
0.7431	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3027	Phase 3
0.7397	Intermediate Similarity	NPD3750	Approved
0.7394	Intermediate Similarity	NPD1607	Approved
0.7391	Intermediate Similarity	NPD6797	Phase 2
0.7391	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1549	Phase 2
0.7372	Intermediate Similarity	NPD1470	Approved
0.7346	Intermediate Similarity	NPD7251	Discontinued
0.7333	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD2932	Approved
0.7312	Intermediate Similarity	NPD3818	Discontinued
0.7303	Intermediate Similarity	NPD4380	Phase 2
0.7301	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD8166	Discontinued
0.7273	Intermediate Similarity	NPD1465	Phase 2
0.7267	Intermediate Similarity	NPD7054	Approved
0.7266	Intermediate Similarity	NPD9494	Approved
0.7254	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1613	Approved
0.7248	Intermediate Similarity	NPD6799	Approved
0.7248	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7075	Discontinued
0.7222	Intermediate Similarity	NPD7074	Phase 3
0.7222	Intermediate Similarity	NPD7472	Approved
0.7195	Intermediate Similarity	NPD7808	Phase 3
0.7185	Intermediate Similarity	NPD3019	Approved
0.7181	Intermediate Similarity	NPD3300	Phase 2
0.7172	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6232	Discontinued
0.7161	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4750	Phase 3
0.7123	Intermediate Similarity	NPD5405	Approved
0.7123	Intermediate Similarity	NPD5406	Approved
0.7123	Intermediate Similarity	NPD5404	Approved
0.7123	Intermediate Similarity	NPD5408	Approved
0.712	Intermediate Similarity	NPD940	Approved
0.712	Intermediate Similarity	NPD846	Approved
0.7113	Intermediate Similarity	NPD3764	Approved
0.7113	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7266	Discontinued
0.7071	Intermediate Similarity	NPD257	Approved
0.7071	Intermediate Similarity	NPD258	Approved
0.7055	Intermediate Similarity	NPD3748	Approved
0.7049	Intermediate Similarity	NPD2933	Approved
0.7049	Intermediate Similarity	NPD2934	Approved
0.7037	Intermediate Similarity	NPD9545	Approved
0.7025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9569	Approved
0.7007	Intermediate Similarity	NPD2796	Approved
0.7007	Intermediate Similarity	NPD6100	Approved
0.7007	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD1164	Approved
0.6992	Remote Similarity	NPD2860	Approved
0.6992	Remote Similarity	NPD2859	Approved
0.6987	Remote Similarity	NPD6801	Discontinued
0.6968	Remote Similarity	NPD6599	Discontinued
0.6963	Remote Similarity	NPD5536	Phase 2
0.696	Remote Similarity	NPD3020	Approved
0.6947	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7819	Suspended
0.6914	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1608	Approved
0.6899	Remote Similarity	NPD5402	Approved
0.6899	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD228	Approved
0.6892	Remote Similarity	NPD9570	Approved
0.6892	Remote Similarity	NPD2935	Discontinued
0.689	Remote Similarity	NPD3751	Discontinued
0.6883	Remote Similarity	NPD5403	Approved
0.6875	Remote Similarity	NPD1237	Approved
0.6875	Remote Similarity	NPD6234	Discontinued
0.6864	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5401	Approved
0.6861	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5844	Phase 1
0.6842	Remote Similarity	NPD9379	Approved
0.6842	Remote Similarity	NPD9377	Approved
0.6833	Remote Similarity	NPD9094	Approved
0.6832	Remote Similarity	NPD5494	Approved
0.6828	Remote Similarity	NPD259	Phase 1
0.6821	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4628	Phase 3
0.6815	Remote Similarity	NPD7411	Suspended
0.6813	Remote Similarity	NPD3749	Approved
0.681	Remote Similarity	NPD3926	Phase 2
0.6806	Remote Similarity	NPD9536	Phase 1
0.6806	Remote Similarity	NPD9537	Phase 1
0.6797	Remote Similarity	NPD4357	Discontinued
0.6795	Remote Similarity	NPD3455	Phase 2
0.6794	Remote Similarity	NPD74	Approved
0.6794	Remote Similarity	NPD9266	Approved
0.679	Remote Similarity	NPD7199	Phase 2
0.6788	Remote Similarity	NPD1548	Phase 1
0.6781	Remote Similarity	NPD825	Approved
0.6781	Remote Similarity	NPD826	Approved
0.6779	Remote Similarity	NPD1551	Phase 2
0.6772	Remote Similarity	NPD37	Approved
0.677	Remote Similarity	NPD919	Approved
0.6763	Remote Similarity	NPD3023	Approved
0.6763	Remote Similarity	NPD3026	Approved
0.6759	Remote Similarity	NPD3268	Approved
0.6755	Remote Similarity	NPD2800	Approved
0.6755	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3025	Approved
0.6739	Remote Similarity	NPD3024	Approved
0.6738	Remote Similarity	NPD1755	Approved
0.6738	Remote Similarity	NPD2983	Phase 2
0.6738	Remote Similarity	NPD2982	Phase 2
0.6735	Remote Similarity	NPD274	Approved
0.6735	Remote Similarity	NPD275	Approved
0.6735	Remote Similarity	NPD555	Phase 2
0.6718	Remote Similarity	NPD9267	Approved
0.6718	Remote Similarity	NPD9264	Approved
0.6718	Remote Similarity	NPD9263	Approved
0.6714	Remote Similarity	NPD1610	Phase 2
0.6714	Remote Similarity	NPD422	Phase 1
0.6712	Remote Similarity	NPD6233	Phase 2
0.6711	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD17	Approved
0.6691	Remote Similarity	NPD9381	Approved
0.6691	Remote Similarity	NPD9384	Approved
0.669	Remote Similarity	NPD3225	Approved
0.669	Remote Similarity	NPD5311	Approved
0.669	Remote Similarity	NPD5310	Approved
0.669	Remote Similarity	NPD7095	Approved
0.6689	Remote Similarity	NPD6651	Approved
0.6687	Remote Similarity	NPD1247	Approved
0.6687	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD2981	Phase 2
0.6667	Remote Similarity	NPD3062	Approved
0.6667	Remote Similarity	NPD3059	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD3061	Approved
0.6667	Remote Similarity	NPD3018	Phase 2
0.6667	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD1481	Phase 2
0.6667	Remote Similarity	NPD2354	Approved
0.6646	Remote Similarity	NPD4965	Approved
0.6646	Remote Similarity	NPD3787	Discontinued
0.6646	Remote Similarity	NPD4966	Approved
0.6646	Remote Similarity	NPD4967	Phase 2
0.6644	Remote Similarity	NPD6798	Discontinued
0.6643	Remote Similarity	NPD2797	Approved
0.6643	Remote Similarity	NPD3055	Approved
0.6643	Remote Similarity	NPD1203	Approved
0.6643	Remote Similarity	NPD3053	Approved
0.6642	Remote Similarity	NPD9493	Approved
0.6624	Remote Similarity	NPD1653	Approved
0.6623	Remote Similarity	NPD2344	Approved
0.6622	Remote Similarity	NPD447	Suspended
0.6621	Remote Similarity	NPD4908	Phase 1
0.6614	Remote Similarity	NPD9495	Approved
0.6596	Remote Similarity	NPD1535	Discovery
0.6587	Remote Similarity	NPD7228	Approved
0.6577	Remote Similarity	NPD5314	Approved
0.6573	Remote Similarity	NPD1283	Approved
0.6566	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5283	Phase 1
0.6543	Remote Similarity	NPD7768	Phase 2
0.6538	Remote Similarity	NPD2532	Approved
0.6538	Remote Similarity	NPD2533	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