NPASS Compound

Structure

NPC472334 OpenBabel07101718282D 26 28 0 0 1 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 1 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 1 1 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:	356.16
Volume:	371.599
LogP:	3.991
LogD:	3.322
LogS:	-4.926
# Rotatable Bonds:	2
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.84
Synthetic Accessibility Score:	5.0
Fsp3:	0.333
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:	-4.827
MDCK Permeability:	1.3496891369868536e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.388
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	99.20508575439453%
Volume Distribution (VD):	0.421
Pgp-substrate:	1.7150208950042725%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.851
CYP2C19-inhibitor:	0.784
CYP2C19-substrate:	0.807
CYP2C9-inhibitor:	0.474
CYP2C9-substrate:	0.521
CYP2D6-inhibitor:	0.283
CYP2D6-substrate:	0.418
CYP3A4-inhibitor:	0.661
CYP3A4-substrate:	0.543

ADMET: Excretion

Clearance (CL):	11.742
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.148
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.169
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.922
Carcinogencity:	0.895
Eye Corrosion:	0.003
Eye Irritation:	0.118
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: NPC472334

Natural Product ID:	NPC472334
*Common Name:**	BYSMYOUCOMWGGJ-IMMZDGJCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BYSMYOUCOMWGGJ-IMMZDGJCSA-N
Standard InCHI:	InChI=1S/C21H24O5/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/h3,5,8-9,11-13,16,22-23H,4,6-7,10H2,1-2H3/b5-3-/t16-/m0/s1
SMILES:	COc1c2/C=CCC[C@H](O)CCc3ccc(Oc(c2)c(c1O)OC)cc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359252
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	=	16.4	%	PMID[458765]
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	28.2	%	PMID[458765]

☑ 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 NPC472334 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	433
0.1-0.2	1582
0.2-0.3	5094
0.3-0.4	12763
0.4-0.5	5022
0.5-0.6	4245
0.6-0.7	6222
0.7-0.8	5491
0.8-0.85	1009
0.85-0.9	567
0.9-0.95	247
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472336
0.9922	High Similarity	NPC472337
0.9771	High Similarity	NPC103976
0.9771	High Similarity	NPC326797
0.9771	High Similarity	NPC474282
0.9771	High Similarity	NPC107551
0.9771	High Similarity	NPC176051
0.9771	High Similarity	NPC102904
0.9767	High Similarity	NPC475840
0.9699	High Similarity	NPC471389
0.9695	High Similarity	NPC16435
0.9695	High Similarity	NPC306441
0.9692	High Similarity	NPC310854
0.9624	High Similarity	NPC160283
0.9624	High Similarity	NPC254759
0.9621	High Similarity	NPC276490
0.9618	High Similarity	NPC61946
0.9618	High Similarity	NPC474206
0.9618	High Similarity	NPC134968
0.9618	High Similarity	NPC112246
0.9618	High Similarity	NPC47398
0.9618	High Similarity	NPC470356
0.9618	High Similarity	NPC94750
0.9618	High Similarity	NPC121812
0.9618	High Similarity	NPC234333
0.9618	High Similarity	NPC260898
0.9618	High Similarity	NPC112939
0.9612	High Similarity	NPC472597
0.9556	High Similarity	NPC477616
0.9552	High Similarity	NPC311530
0.9549	High Similarity	NPC292882
0.9549	High Similarity	NPC127218
0.9549	High Similarity	NPC25966
0.9549	High Similarity	NPC245207
0.9549	High Similarity	NPC319647
0.9549	High Similarity	NPC471388
0.9545	High Similarity	NPC230734
0.9545	High Similarity	NPC269091
0.9545	High Similarity	NPC474639
0.9545	High Similarity	NPC302701
0.9545	High Similarity	NPC227503
0.9542	High Similarity	NPC106215
0.9538	High Similarity	NPC160991
0.9538	High Similarity	NPC16208
0.9538	High Similarity	NPC470752
0.9538	High Similarity	NPC184447
0.9538	High Similarity	NPC7903
0.9538	High Similarity	NPC35932
0.9535	High Similarity	NPC311680
0.9535	High Similarity	NPC234488
0.9535	High Similarity	NPC299221
0.9535	High Similarity	NPC472338
0.9535	High Similarity	NPC214860
0.9535	High Similarity	NPC51840
0.9481	High Similarity	NPC107161
0.9474	High Similarity	NPC211549
0.947	High Similarity	NPC151224
0.947	High Similarity	NPC195022
0.947	High Similarity	NPC164787
0.9466	High Similarity	NPC229442
0.9466	High Similarity	NPC263064
0.9466	High Similarity	NPC168059
0.9466	High Similarity	NPC11060
0.9462	High Similarity	NPC309787
0.9457	High Similarity	NPC470258
0.9457	High Similarity	NPC3439
0.9457	High Similarity	NPC212015
0.9457	High Similarity	NPC285339
0.9457	High Similarity	NPC273295
0.9457	High Similarity	NPC218856
0.9457	High Similarity	NPC476968
0.9457	High Similarity	NPC222004
0.9457	High Similarity	NPC226788
0.9457	High Similarity	NPC58164
0.9457	High Similarity	NPC10225
0.9457	High Similarity	NPC45824
0.9457	High Similarity	NPC170844
0.9457	High Similarity	NPC202582
0.9457	High Similarity	NPC190629
0.9457	High Similarity	NPC210623
0.9407	High Similarity	NPC247291
0.9407	High Similarity	NPC87725
0.9407	High Similarity	NPC263261
0.9398	High Similarity	NPC173660
0.9398	High Similarity	NPC265433
0.9398	High Similarity	NPC270456
0.9398	High Similarity	NPC470802
0.9398	High Similarity	NPC248727
0.9398	High Similarity	NPC162659
0.9398	High Similarity	NPC476698
0.9394	High Similarity	NPC170694
0.9394	High Similarity	NPC317380
0.9389	High Similarity	NPC15658
0.9389	High Similarity	NPC202762
0.9389	High Similarity	NPC127624
0.9389	High Similarity	NPC6451
0.9389	High Similarity	NPC219876
0.9389	High Similarity	NPC86655
0.9389	High Similarity	NPC126029
0.9389	High Similarity	NPC261619
0.9389	High Similarity	NPC253105
0.9389	High Similarity	NPC185604
0.9389	High Similarity	NPC201587
0.9389	High Similarity	NPC61477
0.9389	High Similarity	NPC78770
0.9385	High Similarity	NPC220935
0.938	High Similarity	NPC266691
0.938	High Similarity	NPC206615
0.938	High Similarity	NPC470213
0.938	High Similarity	NPC98631
0.938	High Similarity	NPC186843
0.9343	High Similarity	NPC12641
0.9343	High Similarity	NPC280092
0.9343	High Similarity	NPC50250
0.9343	High Similarity	NPC45257
0.9343	High Similarity	NPC93323
0.9333	High Similarity	NPC259519
0.9333	High Similarity	NPC22317
0.9333	High Similarity	NPC184797
0.9333	High Similarity	NPC27495
0.9333	High Similarity	NPC309124
0.9323	High Similarity	NPC256262
0.9323	High Similarity	NPC281521
0.9323	High Similarity	NPC201357
0.9323	High Similarity	NPC473413
0.9323	High Similarity	NPC255147
0.9313	High Similarity	NPC268342
0.9313	High Similarity	NPC220825
0.9313	High Similarity	NPC232275
0.9313	High Similarity	NPC469613
0.9313	High Similarity	NPC470096
0.9313	High Similarity	NPC474017
0.9313	High Similarity	NPC12275
0.9313	High Similarity	NPC42760
0.9313	High Similarity	NPC474356
0.9313	High Similarity	NPC470095
0.9313	High Similarity	NPC268266
0.9313	High Similarity	NPC469625
0.9313	High Similarity	NPC45715
0.9313	High Similarity	NPC30043
0.9302	High Similarity	NPC147821
0.9302	High Similarity	NPC324112
0.9302	High Similarity	NPC282000
0.9302	High Similarity	NPC183181
0.9302	High Similarity	NPC169474
0.9302	High Similarity	NPC118787
0.9302	High Similarity	NPC210355
0.9302	High Similarity	NPC74817
0.9302	High Similarity	NPC159968
0.9302	High Similarity	NPC111247
0.9302	High Similarity	NPC293054
0.9302	High Similarity	NPC246620
0.9302	High Similarity	NPC41706
0.9302	High Similarity	NPC319625
0.9302	High Similarity	NPC82679
0.9302	High Similarity	NPC163332
0.9302	High Similarity	NPC216836
0.9302	High Similarity	NPC124452
0.9302	High Similarity	NPC474119
0.9302	High Similarity	NPC236791
0.9302	High Similarity	NPC242032
0.9302	High Similarity	NPC292056
0.9281	High Similarity	NPC208507
0.9281	High Similarity	NPC227902
0.9281	High Similarity	NPC472333
0.927	High Similarity	NPC47633
0.927	High Similarity	NPC85264
0.927	High Similarity	NPC102044
0.9259	High Similarity	NPC236306
0.9259	High Similarity	NPC473739
0.9259	High Similarity	NPC260741
0.9259	High Similarity	NPC22517
0.9259	High Similarity	NPC70682
0.9259	High Similarity	NPC232164
0.9254	High Similarity	NPC234952
0.9248	High Similarity	NPC287745
0.9248	High Similarity	NPC478085
0.9237	High Similarity	NPC224157
0.9237	High Similarity	NPC192687
0.9237	High Similarity	NPC469614
0.9237	High Similarity	NPC91291
0.9237	High Similarity	NPC469612
0.9225	High Similarity	NPC58607
0.9225	High Similarity	NPC78974
0.9225	High Similarity	NPC214406
0.9225	High Similarity	NPC223136
0.9225	High Similarity	NPC28730
0.9225	High Similarity	NPC191037
0.9225	High Similarity	NPC103823
0.9225	High Similarity	NPC178284
0.9225	High Similarity	NPC44748
0.9225	High Similarity	NPC18924
0.9214	High Similarity	NPC175976
0.9203	High Similarity	NPC63879
0.9197	High Similarity	NPC472332
0.9197	High Similarity	NPC472335
0.9191	High Similarity	NPC266197
0.9191	High Similarity	NPC291101
0.9185	High Similarity	NPC477938
0.9185	High Similarity	NPC474390

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 NPC472334 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	890
0.2-0.3	2013
0.3-0.4	2732
0.4-0.5	1516
0.5-0.6	865
0.6-0.7	630
0.7-0.8	141
0.8-0.85	7
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9457	High Similarity	NPD3027	Phase 3
0.9389	High Similarity	NPD1612	Clinical (unspecified phase)
0.9389	High Similarity	NPD1613	Approved
0.9084	High Similarity	NPD1529	Clinical (unspecified phase)
0.9008	High Similarity	NPD1530	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1934	Approved
0.8382	Intermediate Similarity	NPD4908	Phase 1
0.8367	Intermediate Similarity	NPD1653	Approved
0.8333	Intermediate Similarity	NPD2801	Approved
0.8309	Intermediate Similarity	NPD2861	Phase 2
0.8271	Intermediate Similarity	NPD1610	Phase 2
0.8261	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD1548	Phase 1
0.8212	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD3018	Phase 2
0.8089	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6166	Phase 2
0.8089	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD2983	Phase 2
0.8015	Intermediate Similarity	NPD2982	Phase 2
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3882	Suspended
0.7984	Intermediate Similarity	NPD228	Approved
0.7941	Intermediate Similarity	NPD2981	Phase 2
0.7929	Intermediate Similarity	NPD4625	Phase 3
0.7888	Intermediate Similarity	NPD7074	Phase 3
0.7883	Intermediate Similarity	NPD4749	Approved
0.7879	Intermediate Similarity	NPD6671	Approved
0.7875	Intermediate Similarity	NPD3818	Discontinued
0.7872	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1091	Approved
0.7863	Intermediate Similarity	NPD5283	Phase 1
0.7852	Intermediate Similarity	NPD1511	Approved
0.7826	Intermediate Similarity	NPD5844	Phase 1
0.7826	Intermediate Similarity	NPD7054	Approved
0.7823	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7472	Approved
0.7771	Intermediate Similarity	NPD6234	Discontinued
0.7762	Intermediate Similarity	NPD1558	Phase 1
0.7762	Intermediate Similarity	NPD4060	Phase 1
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD2684	Approved
0.7748	Intermediate Similarity	NPD1512	Approved
0.7746	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6674	Discontinued
0.7692	Intermediate Similarity	NPD3817	Phase 2
0.7677	Intermediate Similarity	NPD37	Approved
0.7674	Intermediate Similarity	NPD290	Approved
0.7673	Intermediate Similarity	NPD7199	Phase 2
0.7662	Intermediate Similarity	NPD4678	Approved
0.7662	Intermediate Similarity	NPD4675	Approved
0.7652	Intermediate Similarity	NPD7843	Approved
0.7643	Intermediate Similarity	NPD4966	Approved
0.7643	Intermediate Similarity	NPD4965	Approved
0.7643	Intermediate Similarity	NPD4967	Phase 2
0.7639	Intermediate Similarity	NPD3620	Phase 2
0.7639	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6797	Phase 2
0.7612	Intermediate Similarity	NPD7157	Approved
0.761	Intermediate Similarity	NPD5494	Approved
0.7609	Intermediate Similarity	NPD422	Phase 1
0.7603	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4538	Approved
0.7603	Intermediate Similarity	NPD4536	Approved
0.76	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD968	Approved
0.7595	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1652	Phase 2
0.758	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7251	Discontinued
0.7571	Intermediate Similarity	NPD8651	Approved
0.7568	Intermediate Similarity	NPD3540	Phase 1
0.7568	Intermediate Similarity	NPD7266	Discontinued
0.7557	Intermediate Similarity	NPD3022	Approved
0.7557	Intermediate Similarity	NPD3021	Approved
0.7548	Intermediate Similarity	NPD4380	Phase 2
0.7546	Intermediate Similarity	NPD7228	Approved
0.753	Intermediate Similarity	NPD7808	Phase 3
0.7515	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3539	Phase 1
0.75	Intermediate Similarity	NPD7213	Phase 3
0.75	Intermediate Similarity	NPD7212	Phase 2
0.7484	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2677	Approved
0.7482	Intermediate Similarity	NPD3705	Approved
0.7469	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5402	Approved
0.7467	Intermediate Similarity	NPD3060	Approved
0.7467	Intermediate Similarity	NPD5177	Phase 3
0.7466	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD5124	Phase 1
0.7451	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7447	Phase 1
0.745	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6233	Phase 2
0.7432	Intermediate Similarity	NPD5588	Approved
0.7432	Intermediate Similarity	NPD5960	Phase 3
0.7425	Intermediate Similarity	NPD7549	Discontinued
0.7417	Intermediate Similarity	NPD3892	Phase 2
0.741	Intermediate Similarity	NPD3496	Discontinued
0.7405	Intermediate Similarity	NPD1465	Phase 2
0.74	Intermediate Similarity	NPD1549	Phase 2
0.7391	Intermediate Similarity	NPD1357	Approved
0.7379	Intermediate Similarity	NPD6798	Discontinued
0.7376	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7075	Discontinued
0.7372	Intermediate Similarity	NPD4005	Discontinued
0.7368	Intermediate Similarity	NPD6190	Approved
0.7351	Intermediate Similarity	NPD4236	Phase 3
0.7351	Intermediate Similarity	NPD4162	Approved
0.7351	Intermediate Similarity	NPD4237	Approved
0.7347	Intermediate Similarity	NPD6355	Discontinued
0.7343	Intermediate Similarity	NPD6584	Phase 3
0.7338	Intermediate Similarity	NPD4123	Phase 3
0.7338	Intermediate Similarity	NPD6516	Phase 2
0.7338	Intermediate Similarity	NPD5846	Approved
0.7333	Intermediate Similarity	NPD5763	Approved
0.7333	Intermediate Similarity	NPD5762	Approved
0.7324	Intermediate Similarity	NPD6696	Suspended
0.732	Intermediate Similarity	NPD5058	Phase 3
0.7303	Intermediate Similarity	NPD4628	Phase 3
0.7301	Intermediate Similarity	NPD6232	Discontinued
0.7296	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD291	Approved
0.7287	Intermediate Similarity	NPD846	Approved
0.7285	Intermediate Similarity	NPD2424	Discontinued
0.7279	Intermediate Similarity	NPD2238	Phase 2
0.7273	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD1774	Approved
0.7267	Intermediate Similarity	NPD6100	Approved
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7267	Intermediate Similarity	NPD6099	Approved
0.7267	Intermediate Similarity	NPD2796	Approved
0.7262	Intermediate Similarity	NPD6559	Discontinued
0.725	Intermediate Similarity	NPD2563	Approved
0.725	Intermediate Similarity	NPD2560	Approved
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7241	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8053	Approved
0.7235	Intermediate Similarity	NPD8054	Approved
0.7233	Intermediate Similarity	NPD6801	Discontinued
0.723	Intermediate Similarity	NPD230	Phase 1
0.723	Intermediate Similarity	NPD5735	Approved
0.7219	Intermediate Similarity	NPD1375	Discontinued
0.7209	Intermediate Similarity	NPD1242	Phase 1
0.7208	Intermediate Similarity	NPD7124	Phase 2
0.72	Intermediate Similarity	NPD1510	Phase 2
0.72	Intermediate Similarity	NPD7033	Discontinued
0.72	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3686	Approved
0.7197	Intermediate Similarity	NPD3687	Approved
0.7195	Intermediate Similarity	NPD3787	Discontinued
0.7192	Intermediate Similarity	NPD7095	Approved
0.719	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4110	Phase 3
0.719	Intermediate Similarity	NPD6331	Phase 2
0.719	Intermediate Similarity	NPD3750	Approved
0.7188	Intermediate Similarity	NPD2977	Approved
0.7188	Intermediate Similarity	NPD2978	Approved
0.7186	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2231	Phase 2
0.7183	Intermediate Similarity	NPD2235	Phase 2
0.7179	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7164	Intermediate Similarity	NPD4750	Phase 3
0.7162	Intermediate Similarity	NPD1240	Approved
0.7161	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6032	Approved
0.7151	Intermediate Similarity	NPD4663	Approved
0.7143	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2219	Phase 1
0.7134	Intermediate Similarity	NPD1247	Approved
0.7134	Intermediate Similarity	NPD5403	Approved
0.7133	Intermediate Similarity	NPD6583	Phase 3
0.7133	Intermediate Similarity	NPD6582	Phase 2
0.7115	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7906	Approved
0.7108	Intermediate Similarity	NPD27	Approved
0.7108	Intermediate Similarity	NPD2489	Approved
0.7107	Intermediate Similarity	NPD6599	Discontinued
0.7095	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2674	Phase 3
0.7081	Intermediate Similarity	NPD7819	Suspended
0.7081	Intermediate Similarity	NPD5772	Approved
0.7081	Intermediate Similarity	NPD5773	Approved
0.7078	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4535	Phase 3
0.707	Intermediate Similarity	NPD52	Approved
0.707	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7526	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