NPASS Compound

Structure

NPC472335 OpenBabel07101718282D 26 28 0 0 0 0 0 0 0 0999 V2000 -2.7959 0.0123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1584 -1.0922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3067 -1.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9251 -1.6713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1766 -1.0352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5718 -1.6033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6524 -0.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7211 0.0605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5172 1.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5172 -0.7521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9251 0.5200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7211 1.8988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4411 0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5172 0.5200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4411 -0.4412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1350 -1.2782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9251 1.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1766 0.8032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5178 -0.6388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3402 -0.6323 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 2.7500 -1.9612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1257 -1.4701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2541 -0.7302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8945 -0.2117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3067 1.2383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 6 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 17 26 1 0 0 0 0 18 21 2 0 0 0 0 18 26 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	368.962
LogP:	3.444
LogD:	2.924
LogS:	-4.687
# Rotatable Bonds:	2
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.859
Synthetic Accessibility Score:	4.576
Fsp3:	0.286
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:	-4.83
MDCK Permeability:	1.4476024261966813e-05
Pgp-inhibitor:	0.332
Pgp-substrate:	0.263
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	98.52973175048828%
Volume Distribution (VD):	0.411
Pgp-substrate:	1.2576340436935425%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.873
CYP2C19-inhibitor:	0.814
CYP2C19-substrate:	0.734
CYP2C9-inhibitor:	0.625
CYP2C9-substrate:	0.746
CYP2D6-inhibitor:	0.52
CYP2D6-substrate:	0.608
CYP3A4-inhibitor:	0.724
CYP3A4-substrate:	0.459

ADMET: Excretion

Clearance (CL):	9.173
Half-life (T1/2):	0.817

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.147
AMES Toxicity:	0.144
Rat Oral Acute Toxicity:	0.353
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.271
Carcinogencity:	0.847
Eye Corrosion:	0.003
Eye Irritation:	0.071
Respiratory Toxicity:	0.498

Download Data

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

Natural Product: NPC472335

Natural Product ID:	NPC472335
*Common Name:**	HVQRFFWEQMSKPG-HYXAFXHYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HVQRFFWEQMSKPG-HYXAFXHYSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-24-20-15-5-3-4-6-16(22)10-7-14-8-11-17(12-9-14)26-18(13-15)21(25-2)19(20)23/h3,5,8-9,11-13,23H,4,6-7,10H2,1-2H3/b5-3-
SMILES:	COc1c2/C=CCCC(=O)CCc3ccc(Oc(c2)c(c1O)OC)cc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359253
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	=	64.3	%	PMID[528382]
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	63.2	%	PMID[528382]

☑ 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 NPC472335 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	372
0.1-0.2	1491
0.2-0.3	4359
0.3-0.4	11995
0.4-0.5	6124
0.5-0.6	3769
0.6-0.7	5218
0.7-0.8	7029
0.8-0.85	1825
0.85-0.9	498
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472332
0.964	High Similarity	NPC208507
0.964	High Similarity	NPC472333
0.9348	High Similarity	NPC19158
0.9197	High Similarity	NPC472336
0.9197	High Similarity	NPC472334
0.9179	High Similarity	NPC214860
0.9179	High Similarity	NPC51840
0.9179	High Similarity	NPC234488
0.9179	High Similarity	NPC299221
0.9179	High Similarity	NPC311680
0.9161	High Similarity	NPC139839
0.9149	High Similarity	NPC16353
0.913	High Similarity	NPC176051
0.913	High Similarity	NPC276490
0.913	High Similarity	NPC326797
0.913	High Similarity	NPC102904
0.913	High Similarity	NPC474282
0.913	High Similarity	NPC107551
0.913	High Similarity	NPC103976
0.9124	High Similarity	NPC472337
0.9104	High Similarity	NPC58164
0.9104	High Similarity	NPC10225
0.9104	High Similarity	NPC45824
0.9091	High Similarity	NPC165389
0.9065	High Similarity	NPC319647
0.9065	High Similarity	NPC127218
0.9065	High Similarity	NPC245207
0.9065	High Similarity	NPC25966
0.9051	High Similarity	NPC106215
0.9048	High Similarity	NPC145379
0.9048	High Similarity	NPC255350
0.9048	High Similarity	NPC160951
0.9048	High Similarity	NPC274327
0.9048	High Similarity	NPC47781
0.9048	High Similarity	NPC22519
0.9048	High Similarity	NPC176775
0.9048	High Similarity	NPC231018
0.9048	High Similarity	NPC183878
0.9048	High Similarity	NPC69394
0.9044	High Similarity	NPC86655
0.9044	High Similarity	NPC6451
0.9044	High Similarity	NPC202762
0.9044	High Similarity	NPC127624
0.903	High Similarity	NPC266691
0.903	High Similarity	NPC226661
0.9021	High Similarity	NPC474799
0.9	High Similarity	NPC160283
0.9	High Similarity	NPC254759
0.8993	High Similarity	NPC78225
0.8993	High Similarity	NPC162869
0.8993	High Similarity	NPC472913
0.8993	High Similarity	NPC48208
0.8993	High Similarity	NPC472914
0.8993	High Similarity	NPC474836
0.8993	High Similarity	NPC245758
0.8993	High Similarity	NPC222814
0.8993	High Similarity	NPC474208
0.8993	High Similarity	NPC472911
0.8993	High Similarity	NPC96167
0.8993	High Similarity	NPC475267
0.8993	High Similarity	NPC156057
0.8993	High Similarity	NPC472910
0.8986	High Similarity	NPC256612
0.8986	High Similarity	NPC4455
0.8986	High Similarity	NPC20830
0.8986	High Similarity	NPC2476
0.8986	High Similarity	NPC195022
0.8986	High Similarity	NPC50715
0.8986	High Similarity	NPC146165
0.8986	High Similarity	NPC138360
0.8986	High Similarity	NPC280339
0.8986	High Similarity	NPC474206
0.8986	High Similarity	NPC255147
0.8986	High Similarity	NPC470356
0.8986	High Similarity	NPC201357
0.8986	High Similarity	NPC183597
0.8986	High Similarity	NPC94750
0.8986	High Similarity	NPC152209
0.8986	High Similarity	NPC163780
0.8986	High Similarity	NPC121812
0.8986	High Similarity	NPC134968
0.8986	High Similarity	NPC112939
0.8986	High Similarity	NPC92659
0.8986	High Similarity	NPC281521
0.8986	High Similarity	NPC201136
0.8986	High Similarity	NPC128863
0.8986	High Similarity	NPC213622
0.8986	High Similarity	NPC196439
0.8986	High Similarity	NPC227325
0.8986	High Similarity	NPC112246
0.8986	High Similarity	NPC167815
0.898	High Similarity	NPC162313
0.898	High Similarity	NPC239128
0.898	High Similarity	NPC25270
0.898	High Similarity	NPC57030
0.898	High Similarity	NPC120163
0.898	High Similarity	NPC187498
0.898	High Similarity	NPC198826
0.898	High Similarity	NPC275722
0.898	High Similarity	NPC100887
0.898	High Similarity	NPC212678
0.898	High Similarity	NPC275836
0.898	High Similarity	NPC293183
0.898	High Similarity	NPC188203
0.898	High Similarity	NPC71334
0.898	High Similarity	NPC301323
0.898	High Similarity	NPC120537
0.898	High Similarity	NPC199100
0.898	High Similarity	NPC222830
0.898	High Similarity	NPC83508
0.898	High Similarity	NPC256283
0.898	High Similarity	NPC131624
0.898	High Similarity	NPC156222
0.898	High Similarity	NPC180234
0.898	High Similarity	NPC241498
0.8978	High Similarity	NPC229442
0.8978	High Similarity	NPC475840
0.8978	High Similarity	NPC168059
0.8971	High Similarity	NPC232275
0.8971	High Similarity	NPC45715
0.8971	High Similarity	NPC474356
0.8971	High Similarity	NPC12275
0.8955	High Similarity	NPC293054
0.8955	High Similarity	NPC169474
0.8955	High Similarity	NPC82679
0.8955	High Similarity	NPC124452
0.8955	High Similarity	NPC216836
0.8955	High Similarity	NPC324112
0.8955	High Similarity	NPC159968
0.8955	High Similarity	NPC236791
0.8955	High Similarity	NPC246620
0.8955	High Similarity	NPC282000
0.8955	High Similarity	NPC74817
0.8955	High Similarity	NPC210355
0.8951	High Similarity	NPC474982
0.8951	High Similarity	NPC207732
0.8944	High Similarity	NPC91492
0.8944	High Similarity	NPC7439
0.8944	High Similarity	NPC256555
0.8944	High Similarity	NPC110067
0.8944	High Similarity	NPC34245
0.8936	High Similarity	NPC471389
0.8929	High Similarity	NPC292882
0.8926	High Similarity	NPC472916
0.8926	High Similarity	NPC191146
0.8926	High Similarity	NPC49824
0.8926	High Similarity	NPC255106
0.8926	High Similarity	NPC68093
0.8926	High Similarity	NPC235165
0.8921	High Similarity	NPC173660
0.8921	High Similarity	NPC306441
0.8921	High Similarity	NPC474639
0.8921	High Similarity	NPC265433
0.8921	High Similarity	NPC270456
0.8921	High Similarity	NPC248727
0.8921	High Similarity	NPC162659
0.8921	High Similarity	NPC227503
0.8921	High Similarity	NPC230734
0.8921	High Similarity	NPC16435
0.8919	High Similarity	NPC276409
0.8919	High Similarity	NPC75279
0.8919	High Similarity	NPC292214
0.8919	High Similarity	NPC88645
0.8919	High Similarity	NPC206238
0.8919	High Similarity	NPC167091
0.8919	High Similarity	NPC250822
0.8919	High Similarity	NPC271779
0.8919	High Similarity	NPC18727
0.8913	High Similarity	NPC317380
0.8913	High Similarity	NPC310854
0.8912	High Similarity	NPC117579
0.8912	High Similarity	NPC308451
0.8912	High Similarity	NPC226973
0.8912	High Similarity	NPC208043
0.8904	High Similarity	NPC177298
0.8904	High Similarity	NPC223579
0.8904	High Similarity	NPC183950
0.8904	High Similarity	NPC287101
0.8904	High Similarity	NPC328119
0.8904	High Similarity	NPC200221
0.8904	High Similarity	NPC48479
0.8904	High Similarity	NPC102003
0.8904	High Similarity	NPC137062
0.8904	High Similarity	NPC92722
0.8904	High Similarity	NPC52005
0.8904	High Similarity	NPC294502
0.8897	High Similarity	NPC192687
0.8897	High Similarity	NPC220935
0.8897	High Similarity	NPC224157
0.8889	High Similarity	NPC157133
0.8881	High Similarity	NPC103823
0.8881	High Similarity	NPC28730
0.8881	High Similarity	NPC214406
0.8881	High Similarity	NPC44748
0.8881	High Similarity	NPC18924
0.8881	High Similarity	NPC78974
0.8881	High Similarity	NPC223136
0.8874	High Similarity	NPC476980
0.8873	High Similarity	NPC110419

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 NPC472335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	892
0.2-0.3	1743
0.3-0.4	2715
0.4-0.5	1746
0.5-0.6	939
0.6-0.7	629
0.7-0.8	141
0.8-0.85	13
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD2801	Approved
0.8851	High Similarity	NPD1934	Approved
0.875	High Similarity	NPD1529	Clinical (unspecified phase)
0.8686	High Similarity	NPD3027	Phase 3
0.8676	High Similarity	NPD1530	Clinical (unspecified phase)
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8633	High Similarity	NPD1613	Approved
0.8633	High Similarity	NPD1612	Clinical (unspecified phase)
0.8562	High Similarity	NPD1511	Approved
0.8553	High Similarity	NPD3882	Suspended
0.8446	Intermediate Similarity	NPD1512	Approved
0.8408	Intermediate Similarity	NPD6166	Phase 2
0.8408	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD3817	Phase 2
0.8227	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7074	Phase 3
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.8137	Intermediate Similarity	NPD7054	Approved
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6234	Discontinued
0.8086	Intermediate Similarity	NPD7472	Approved
0.8049	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5494	Approved
0.8025	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD7199	Phase 2
0.7974	Intermediate Similarity	NPD1653	Approved
0.7959	Intermediate Similarity	NPD6100	Approved
0.7959	Intermediate Similarity	NPD6099	Approved
0.7958	Intermediate Similarity	NPD4908	Phase 1
0.7949	Intermediate Similarity	NPD1465	Phase 2
0.7927	Intermediate Similarity	NPD6797	Phase 2
0.7905	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD3018	Phase 2
0.7885	Intermediate Similarity	NPD37	Approved
0.7879	Intermediate Similarity	NPD7251	Discontinued
0.7871	Intermediate Similarity	NPD4380	Phase 2
0.7867	Intermediate Similarity	NPD3750	Approved
0.7862	Intermediate Similarity	NPD1240	Approved
0.7852	Intermediate Similarity	NPD1549	Phase 2
0.7848	Intermediate Similarity	NPD4966	Approved
0.7848	Intermediate Similarity	NPD4965	Approved
0.7848	Intermediate Similarity	NPD4967	Phase 2
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1610	Phase 2
0.7838	Intermediate Similarity	NPD2935	Discontinued
0.7831	Intermediate Similarity	NPD7808	Phase 3
0.7829	Intermediate Similarity	NPD6799	Approved
0.7826	Intermediate Similarity	NPD6232	Discontinued
0.7818	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1548	Phase 1
0.7799	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7075	Discontinued
0.7793	Intermediate Similarity	NPD6233	Phase 2
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.7785	Intermediate Similarity	NPD5402	Approved
0.777	Intermediate Similarity	NPD1510	Phase 2
0.7762	Intermediate Similarity	NPD2861	Phase 2
0.7755	Intermediate Similarity	NPD1607	Approved
0.7744	Intermediate Similarity	NPD7228	Approved
0.774	Intermediate Similarity	NPD943	Approved
0.773	Intermediate Similarity	NPD2982	Phase 2
0.773	Intermediate Similarity	NPD2983	Phase 2
0.7724	Intermediate Similarity	NPD6798	Discontinued
0.7722	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2796	Approved
0.7712	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6355	Discontinued
0.7687	Intermediate Similarity	NPD230	Phase 1
0.7687	Intermediate Similarity	NPD228	Approved
0.7677	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD2981	Phase 2
0.7655	Intermediate Similarity	NPD4625	Phase 3
0.7654	Intermediate Similarity	NPD1247	Approved
0.7643	Intermediate Similarity	NPD6599	Discontinued
0.7632	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4060	Phase 1
0.7613	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7819	Suspended
0.7609	Intermediate Similarity	NPD5536	Phase 2
0.7606	Intermediate Similarity	NPD4749	Approved
0.7591	Intermediate Similarity	NPD6671	Approved
0.7589	Intermediate Similarity	NPD422	Phase 1
0.7589	Intermediate Similarity	NPD1535	Discovery
0.7582	Intermediate Similarity	NPD6190	Approved
0.7574	Intermediate Similarity	NPD5283	Phase 1
0.7568	Intermediate Similarity	NPD447	Suspended
0.7562	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3926	Phase 2
0.756	Intermediate Similarity	NPD6559	Discontinued
0.7547	Intermediate Similarity	NPD6801	Discontinued
0.7535	Intermediate Similarity	NPD1481	Phase 2
0.7535	Intermediate Similarity	NPD1608	Approved
0.7533	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1558	Phase 1
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4357	Discontinued
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7411	Suspended
0.7483	Intermediate Similarity	NPD1551	Phase 2
0.7483	Intermediate Similarity	NPD3268	Approved
0.7452	Intermediate Similarity	NPD5403	Approved
0.7451	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6959	Discontinued
0.7423	Intermediate Similarity	NPD919	Approved
0.7415	Intermediate Similarity	NPD7095	Approved
0.7407	Intermediate Similarity	NPD7768	Phase 2
0.7397	Intermediate Similarity	NPD9494	Approved
0.7384	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2800	Approved
0.7325	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5401	Approved
0.7324	Intermediate Similarity	NPD17	Approved
0.7321	Intermediate Similarity	NPD3751	Discontinued
0.732	Intermediate Similarity	NPD3540	Phase 1
0.7315	Intermediate Similarity	NPD4062	Phase 3
0.7312	Intermediate Similarity	NPD4678	Approved
0.7312	Intermediate Similarity	NPD4675	Approved
0.731	Intermediate Similarity	NPD7549	Discontinued
0.7303	Intermediate Similarity	NPD7033	Discontinued
0.7296	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7279	Intermediate Similarity	NPD3021	Approved
0.7279	Intermediate Similarity	NPD3022	Approved
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7273	Intermediate Similarity	NPD3496	Discontinued
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3539	Phase 1
0.7254	Intermediate Similarity	NPD1651	Approved
0.7251	Intermediate Similarity	NPD7240	Approved
0.7248	Intermediate Similarity	NPD1296	Phase 2
0.7244	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1652	Phase 2
0.7225	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1091	Approved
0.7219	Intermediate Similarity	NPD1933	Approved
0.7215	Intermediate Similarity	NPD2533	Approved
0.7215	Intermediate Similarity	NPD2534	Approved
0.7215	Intermediate Similarity	NPD2532	Approved
0.7208	Intermediate Similarity	NPD7266	Discontinued
0.7206	Intermediate Similarity	NPD2684	Approved
0.7203	Intermediate Similarity	NPD1778	Approved
0.7202	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3225	Approved
0.719	Intermediate Similarity	NPD2799	Discontinued
0.719	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD968	Approved
0.7183	Intermediate Similarity	NPD1894	Discontinued
0.7179	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8455	Phase 2
0.7152	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD6032	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD1203	Approved
0.7143	Intermediate Similarity	NPD5242	Approved
0.7134	Intermediate Similarity	NPD2219	Phase 1
0.7126	Intermediate Similarity	NPD8127	Discontinued
0.7123	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7843	Approved
0.7115	Intermediate Similarity	NPD6674	Discontinued
0.7107	Intermediate Similarity	NPD7447	Phase 1
0.7105	Intermediate Similarity	NPD5124	Phase 1
0.7105	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3705	Approved
0.7097	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2344	Approved
0.7097	Intermediate Similarity	NPD6004	Phase 3
0.7097	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6002	Phase 3
0.7097	Intermediate Similarity	NPD6005	Phase 3
0.7095	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7157	Approved
0.7078	Intermediate Similarity	NPD4308	Phase 3
0.7075	Intermediate Similarity	NPD1283	Approved
0.7075	Intermediate Similarity	NPD8651	Approved
0.7075	Intermediate Similarity	NPD6696	Suspended
0.7071	Intermediate Similarity	NPD1241	Discontinued
0.707	Intermediate Similarity	NPD8166	Discontinued
0.7066	Intermediate Similarity	NPD6746	Phase 2
0.7059	Intermediate Similarity	NPD6653	Approved
0.7059	Intermediate Similarity	NPD6651	Approved
0.7055	Intermediate Similarity	NPD9269	Phase 2
0.7051	Intermediate Similarity	NPD4534	Discontinued
0.7048	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6971	Discontinued
0.7044	Intermediate Similarity	NPD7213	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data