NPASS Compound

Structure

NPC472338 OpenBabel07101718282D 24 26 0 0 1 0 0 0 0 0999 V2000 2.4890 1.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.3518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5098 -2.5629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3902 -1.9616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0616 -2.5629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1727 -1.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2759 -1.3423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2381 0.0979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9616 -1.9616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4444 -0.7867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4067 0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5821 -1.6469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6013 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1727 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6013 -1.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5714 -2.3518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5098 0.2112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8283 -0.8166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3902 -0.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2323 -0.1882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1270 -3.1832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8007 -0.5834 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5166 0.7705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 1 0 0 0 0 2 4 2 0 0 0 0 3 5 2 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 16 21 1 6 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.14
Volume:	342.876
LogP:	3.747
LogD:	3.243
LogS:	-5.043
# Rotatable Bonds:	1
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.83
Synthetic Accessibility Score:	5.163
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.938
MDCK Permeability:	1.3457205568556674e-05
Pgp-inhibitor:	0.134
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	98.570068359375%
Volume Distribution (VD):	0.467
Pgp-substrate:	1.721191167831421%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.725
CYP2C19-inhibitor:	0.903
CYP2C19-substrate:	0.362
CYP2C9-inhibitor:	0.774
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.771
CYP2D6-substrate:	0.771
CYP3A4-inhibitor:	0.816
CYP3A4-substrate:	0.556

ADMET: Excretion

Clearance (CL):	9.778
Half-life (T1/2):	0.32

ADMET: Toxicity

hERG Blockers:	0.67
Human Hepatotoxicity (H-HT):	0.708
Drug-inuced Liver Injury (DILI):	0.46
AMES Toxicity:	0.83
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.946
Carcinogencity:	0.291
Eye Corrosion:	0.003
Eye Irritation:	0.401
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC472338

Natural Product ID:	NPC472338
*Common Name:**	ZEZGBCQEBHRYPA-JGSLLADXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZEZGBCQEBHRYPA-JGSLLADXSA-N
Standard InCHI:	InChI=1S/C20H20O4/c1-23-20-18(22)12-15-4-2-3-5-16(21)9-6-14-7-10-17(11-8-14)24-19(20)13-15/h2-5,7-8,10-13,16,21-22H,6,9H2,1H3/b4-2-,5-3+/t16-/m0/s1
SMILES:	COC1=C(C=C2C=CC=CC(CCC3=CC=C(C=C3)OC1=C2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359257
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003523] Meta,para-diphenylether diarylheptanoids

*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
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Shells; Leaves	n.a.	n.a.	PMID[18163585]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25420236]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26606246]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Green Leafy Covers	n.a.	n.a.	PMID[28520428]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12631	Corylus avellana	Species	Betulaceae	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
Others	2

Activity Type	# Activity
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	55.8	%	PMID[536430]
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	50.6	%	PMID[536430]

☑ 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 NPC472338 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	396
0.1-0.2	1536
0.2-0.3	5264
0.3-0.4	12941
0.4-0.5	4677
0.5-0.6	4506
0.6-0.7	6868
0.7-0.8	4781
0.8-0.85	1021
0.85-0.9	458
0.9-0.95	207
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC472597
0.984	High Similarity	NPC160991
0.984	High Similarity	NPC184447
0.984	High Similarity	NPC7903
0.984	High Similarity	NPC35932
0.984	High Similarity	NPC16208
0.9762	High Similarity	NPC475840
0.9758	High Similarity	NPC190629
0.9758	High Similarity	NPC273295
0.9758	High Similarity	NPC202582
0.9758	High Similarity	NPC285339
0.9758	High Similarity	NPC218856
0.9758	High Similarity	NPC222004
0.9758	High Similarity	NPC3439
0.9758	High Similarity	NPC210623
0.9758	High Similarity	NPC226788
0.9758	High Similarity	NPC470258
0.9756	High Similarity	NPC210355
0.9756	High Similarity	NPC474119
0.9685	High Similarity	NPC310854
0.9685	High Similarity	NPC170694
0.9683	High Similarity	NPC470752
0.9677	High Similarity	NPC206615
0.9677	High Similarity	NPC470213
0.9677	High Similarity	NPC98631
0.9677	High Similarity	NPC186843
0.9609	High Similarity	NPC472337
0.9603	High Similarity	NPC469613
0.9603	High Similarity	NPC309787
0.9603	High Similarity	NPC470096
0.9603	High Similarity	NPC30043
0.9603	High Similarity	NPC469625
0.9603	High Similarity	NPC470095
0.96	High Similarity	NPC170844
0.96	High Similarity	NPC476968
0.9597	High Similarity	NPC183181
0.9597	High Similarity	NPC111247
0.9597	High Similarity	NPC118787
0.9597	High Similarity	NPC163332
0.9597	High Similarity	NPC41706
0.9597	High Similarity	NPC147821
0.9597	High Similarity	NPC319625
0.9597	High Similarity	NPC292056
0.9593	High Similarity	NPC194519
0.9535	High Similarity	NPC472336
0.9535	High Similarity	NPC16435
0.9535	High Similarity	NPC306441
0.9535	High Similarity	NPC472334
0.9528	High Similarity	NPC201587
0.9528	High Similarity	NPC253105
0.9524	High Similarity	NPC469614
0.9524	High Similarity	NPC469612
0.9516	High Similarity	NPC191037
0.9516	High Similarity	NPC58607
0.9516	High Similarity	NPC178284
0.9512	High Similarity	NPC293701
0.9512	High Similarity	NPC114901
0.9512	High Similarity	NPC228972
0.9512	High Similarity	NPC48990
0.9512	High Similarity	NPC122792
0.9457	High Similarity	NPC121812
0.9457	High Similarity	NPC112939
0.9457	High Similarity	NPC260898
0.9457	High Similarity	NPC94750
0.9457	High Similarity	NPC61946
0.9457	High Similarity	NPC112246
0.9457	High Similarity	NPC47398
0.9457	High Similarity	NPC234333
0.9457	High Similarity	NPC470356
0.9457	High Similarity	NPC474206
0.9453	High Similarity	NPC168059
0.9453	High Similarity	NPC229442
0.9449	High Similarity	NPC474017
0.9444	High Similarity	NPC86030
0.9444	High Similarity	NPC212015
0.9444	High Similarity	NPC5851
0.944	High Similarity	NPC470699
0.9435	High Similarity	NPC17943
0.9435	High Similarity	NPC208950
0.9435	High Similarity	NPC251855
0.9435	High Similarity	NPC193544
0.9435	High Similarity	NPC221077
0.9435	High Similarity	NPC116907
0.9435	High Similarity	NPC298757
0.9435	High Similarity	NPC203133
0.9435	High Similarity	NPC233410
0.9435	High Similarity	NPC57490
0.9435	High Similarity	NPC117214
0.9435	High Similarity	NPC472093
0.9435	High Similarity	NPC475169
0.9389	High Similarity	NPC22517
0.9385	High Similarity	NPC474639
0.9385	High Similarity	NPC269091
0.9385	High Similarity	NPC227503
0.9385	High Similarity	NPC302701
0.9385	High Similarity	NPC230734
0.938	High Similarity	NPC317380
0.938	High Similarity	NPC287745
0.937	High Similarity	NPC91291
0.9365	High Similarity	NPC72529
0.936	High Similarity	NPC78974
0.936	High Similarity	NPC18924
0.936	High Similarity	NPC214406
0.936	High Similarity	NPC44748
0.936	High Similarity	NPC103823
0.936	High Similarity	NPC223136
0.936	High Similarity	NPC181361
0.936	High Similarity	NPC28730
0.9355	High Similarity	NPC94276
0.9355	High Similarity	NPC109822
0.935	High Similarity	NPC71090
0.935	High Similarity	NPC262253
0.935	High Similarity	NPC261661
0.935	High Similarity	NPC71579
0.935	High Similarity	NPC473411
0.9318	High Similarity	NPC267291
0.9318	High Similarity	NPC266197
0.9318	High Similarity	NPC291101
0.9313	High Similarity	NPC107551
0.9313	High Similarity	NPC102904
0.9313	High Similarity	NPC474390
0.9313	High Similarity	NPC211549
0.9313	High Similarity	NPC326797
0.9313	High Similarity	NPC474282
0.9313	High Similarity	NPC176051
0.9313	High Similarity	NPC103976
0.9308	High Similarity	NPC151224
0.9308	High Similarity	NPC164787
0.9302	High Similarity	NPC263064
0.9302	High Similarity	NPC158331
0.9302	High Similarity	NPC11060
0.9286	High Similarity	NPC236791
0.9286	High Similarity	NPC169474
0.9286	High Similarity	NPC159968
0.9286	High Similarity	NPC293054
0.9286	High Similarity	NPC324112
0.9286	High Similarity	NPC124452
0.9286	High Similarity	NPC127587
0.9286	High Similarity	NPC246620
0.9286	High Similarity	NPC82679
0.9286	High Similarity	NPC74817
0.9286	High Similarity	NPC282000
0.928	High Similarity	NPC60885
0.928	High Similarity	NPC234400
0.928	High Similarity	NPC299584
0.928	High Similarity	NPC82483
0.928	High Similarity	NPC265483
0.9274	High Similarity	NPC136319
0.9274	High Similarity	NPC233526
0.9274	High Similarity	NPC471693
0.9274	High Similarity	NPC197757
0.9274	High Similarity	NPC165375
0.9274	High Similarity	NPC282496
0.9274	High Similarity	NPC220598
0.9274	High Similarity	NPC228922
0.9268	High Similarity	NPC145780
0.9268	High Similarity	NPC49341
0.9248	High Similarity	NPC83375
0.9248	High Similarity	NPC471389
0.9248	High Similarity	NPC87725
0.9248	High Similarity	NPC224876
0.9248	High Similarity	NPC263261
0.9237	High Similarity	NPC162659
0.9237	High Similarity	NPC265433
0.9237	High Similarity	NPC248727
0.9237	High Similarity	NPC270456
0.9237	High Similarity	NPC25695
0.9237	High Similarity	NPC172818
0.9237	High Similarity	NPC470802
0.9237	High Similarity	NPC471719
0.9231	High Similarity	NPC244983
0.9231	High Similarity	NPC478085
0.9231	High Similarity	NPC326095
0.9225	High Similarity	NPC15658
0.9225	High Similarity	NPC219876
0.9225	High Similarity	NPC126029
0.9225	High Similarity	NPC175067
0.9225	High Similarity	NPC86655
0.9225	High Similarity	NPC202762
0.9225	High Similarity	NPC185604
0.9225	High Similarity	NPC204215
0.9225	High Similarity	NPC78770
0.9225	High Similarity	NPC261619
0.9225	High Similarity	NPC127624
0.9225	High Similarity	NPC61477
0.9219	High Similarity	NPC214860
0.9213	High Similarity	NPC252307
0.9213	High Similarity	NPC245826
0.9213	High Similarity	NPC474178
0.9206	High Similarity	NPC76451
0.9194	High Similarity	NPC41562
0.9187	High Similarity	NPC199023
0.9187	High Similarity	NPC166759
0.9187	High Similarity	NPC472596
0.9179	High Similarity	NPC193722
0.9179	High Similarity	NPC189115
0.9179	High Similarity	NPC278469
0.9179	High Similarity	NPC469559
0.9173	High Similarity	NPC160283
0.9173	High Similarity	NPC254759

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 NPC472338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	882
0.2-0.3	1927
0.3-0.4	2735
0.4-0.5	1569
0.5-0.6	924
0.6-0.7	621
0.7-0.8	156
0.8-0.85	8
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.96	High Similarity	NPD3027	Phase 3
0.9225	High Similarity	NPD1612	Clinical (unspecified phase)
0.9225	High Similarity	NPD1613	Approved
0.8915	High Similarity	NPD1529	Clinical (unspecified phase)
0.8837	High Similarity	NPD1530	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD2983	Phase 2
0.8385	Intermediate Similarity	NPD2982	Phase 2
0.8374	Intermediate Similarity	NPD228	Approved
0.8346	Intermediate Similarity	NPD4908	Phase 1
0.8346	Intermediate Similarity	NPD1548	Phase 1
0.8308	Intermediate Similarity	NPD2981	Phase 2
0.8271	Intermediate Similarity	NPD3018	Phase 2
0.8231	Intermediate Similarity	NPD1934	Approved
0.8231	Intermediate Similarity	NPD1610	Phase 2
0.8222	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD1558	Phase 1
0.8095	Intermediate Similarity	NPD5283	Phase 1
0.8082	Intermediate Similarity	NPD1653	Approved
0.8067	Intermediate Similarity	NPD3882	Suspended
0.8054	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD2801	Approved
0.7984	Intermediate Similarity	NPD2684	Approved
0.7935	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6166	Phase 2
0.7883	Intermediate Similarity	NPD4625	Phase 3
0.7874	Intermediate Similarity	NPD7843	Approved
0.7868	Intermediate Similarity	NPD2861	Phase 2
0.7852	Intermediate Similarity	NPD4678	Approved
0.7852	Intermediate Similarity	NPD4675	Approved
0.7842	Intermediate Similarity	NPD3620	Phase 2
0.7842	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4749	Approved
0.7829	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7157	Approved
0.7826	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1091	Approved
0.7808	Intermediate Similarity	NPD1511	Approved
0.7785	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD3022	Approved
0.7778	Intermediate Similarity	NPD3060	Approved
0.7778	Intermediate Similarity	NPD3021	Approved
0.7762	Intermediate Similarity	NPD7266	Discontinued
0.776	Intermediate Similarity	NPD290	Approved
0.7736	Intermediate Similarity	NPD7074	Phase 3
0.7736	Intermediate Similarity	NPD7472	Approved
0.7727	Intermediate Similarity	NPD6234	Discontinued
0.7727	Intermediate Similarity	NPD1357	Approved
0.7722	Intermediate Similarity	NPD3818	Discontinued
0.7714	Intermediate Similarity	NPD4060	Phase 1
0.7703	Intermediate Similarity	NPD1512	Approved
0.7687	Intermediate Similarity	NPD422	Phase 1
0.7687	Intermediate Similarity	NPD3705	Approved
0.7676	Intermediate Similarity	NPD4538	Approved
0.7676	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD4536	Approved
0.7671	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD4162	Approved
0.7655	Intermediate Similarity	NPD4236	Phase 3
0.7655	Intermediate Similarity	NPD4237	Approved
0.7655	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3817	Phase 2
0.7642	Intermediate Similarity	NPD291	Approved
0.7639	Intermediate Similarity	NPD3540	Phase 1
0.7632	Intermediate Similarity	NPD37	Approved
0.7628	Intermediate Similarity	NPD7199	Phase 2
0.7597	Intermediate Similarity	NPD4966	Approved
0.7597	Intermediate Similarity	NPD4965	Approved
0.7597	Intermediate Similarity	NPD4967	Phase 2
0.7578	Intermediate Similarity	NPD6797	Phase 2
0.7576	Intermediate Similarity	NPD5536	Phase 2
0.7569	Intermediate Similarity	NPD3539	Phase 1
0.7568	Intermediate Similarity	NPD4357	Discontinued
0.7561	Intermediate Similarity	NPD1242	Phase 1
0.7554	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4005	Discontinued
0.754	Intermediate Similarity	NPD968	Approved
0.7537	Intermediate Similarity	NPD5846	Approved
0.7537	Intermediate Similarity	NPD6516	Phase 2
0.7536	Intermediate Similarity	NPD6584	Phase 3
0.7536	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6674	Discontinued
0.7534	Intermediate Similarity	NPD1652	Phase 2
0.7531	Intermediate Similarity	NPD7251	Discontinued
0.7518	Intermediate Similarity	NPD8651	Approved
0.7517	Intermediate Similarity	NPD4123	Phase 3
0.75	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD5960	Phase 3
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7808	Phase 3
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7453	Intermediate Similarity	NPD5844	Phase 1
0.745	Intermediate Similarity	NPD7212	Phase 2
0.745	Intermediate Similarity	NPD7213	Phase 3
0.7436	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2677	Approved
0.7432	Intermediate Similarity	NPD6190	Approved
0.7424	Intermediate Similarity	NPD6671	Approved
0.7421	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5735	Approved
0.7413	Intermediate Similarity	NPD5124	Phase 1
0.7413	Intermediate Similarity	NPD230	Phase 1
0.74	Intermediate Similarity	NPD7447	Phase 1
0.7397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6233	Phase 2
0.7394	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2674	Phase 3
0.7386	Intermediate Similarity	NPD4380	Phase 2
0.7383	Intermediate Similarity	NPD7124	Phase 2
0.7383	Intermediate Similarity	NPD5058	Phase 3
0.7376	Intermediate Similarity	NPD7095	Approved
0.7372	Intermediate Similarity	NPD2231	Phase 2
0.7372	Intermediate Similarity	NPD2235	Phase 2
0.7368	Intermediate Similarity	NPD3687	Approved
0.7368	Intermediate Similarity	NPD3686	Approved
0.7365	Intermediate Similarity	NPD4110	Phase 3
0.7365	Intermediate Similarity	NPD3892	Phase 2
0.7365	Intermediate Similarity	NPD6331	Phase 2
0.7365	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2978	Approved
0.7355	Intermediate Similarity	NPD2977	Approved
0.7351	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1549	Phase 2
0.7333	Intermediate Similarity	NPD6799	Approved
0.7333	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7075	Discontinued
0.7324	Intermediate Similarity	NPD6798	Discontinued
0.7319	Intermediate Similarity	NPD6583	Phase 3
0.7319	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6582	Phase 2
0.7315	Intermediate Similarity	NPD2219	Phase 1
0.7297	Intermediate Similarity	NPD5177	Phase 3
0.7292	Intermediate Similarity	NPD4340	Discontinued
0.7292	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1375	Discontinued
0.7279	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5763	Approved
0.7279	Intermediate Similarity	NPD5762	Approved
0.7273	Intermediate Similarity	NPD4062	Phase 3
0.7254	Intermediate Similarity	NPD3179	Approved
0.7254	Intermediate Similarity	NPD3180	Approved
0.7244	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5773	Approved
0.7244	Intermediate Similarity	NPD5772	Approved
0.7244	Intermediate Similarity	NPD1465	Phase 2
0.7241	Intermediate Similarity	NPD3052	Approved
0.7241	Intermediate Similarity	NPD6653	Approved
0.7241	Intermediate Similarity	NPD3054	Approved
0.7234	Intermediate Similarity	NPD9494	Approved
0.7233	Intermediate Similarity	NPD5494	Approved
0.7222	Intermediate Similarity	NPD2238	Phase 2
0.7222	Intermediate Similarity	NPD846	Approved
0.7222	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD940	Approved
0.7219	Intermediate Similarity	NPD1774	Approved
0.7211	Intermediate Similarity	NPD2161	Phase 2
0.7211	Intermediate Similarity	NPD6099	Approved
0.7211	Intermediate Similarity	NPD2796	Approved
0.7211	Intermediate Similarity	NPD6100	Approved
0.7203	Intermediate Similarity	NPD3144	Approved
0.7203	Intermediate Similarity	NPD3145	Approved
0.72	Intermediate Similarity	NPD5241	Discontinued
0.7197	Intermediate Similarity	NPD2560	Approved
0.7197	Intermediate Similarity	NPD5402	Approved
0.7197	Intermediate Similarity	NPD2563	Approved
0.7197	Intermediate Similarity	NPD821	Approved
0.7197	Intermediate Similarity	NPD5535	Approved
0.7192	Intermediate Similarity	NPD6111	Discontinued
0.719	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5403	Approved
0.7186	Intermediate Similarity	NPD8053	Approved
0.7186	Intermediate Similarity	NPD8054	Approved
0.7179	Intermediate Similarity	NPD6801	Discontinued
0.7171	Intermediate Similarity	NPD3536	Discontinued
0.7154	Intermediate Similarity	NPD9296	Approved
0.7154	Intermediate Similarity	NPD2934	Approved
0.7154	Intermediate Similarity	NPD2933	Approved
0.7143	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7133	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4535	Phase 3
0.7133	Intermediate Similarity	NPD3750	Approved
0.7124	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD52	Approved
0.7124	Intermediate Similarity	NPD7526	Approved
0.7122	Intermediate Similarity	NPD1608	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