NPASS Compound

Structure

NPC472339 OpenBabel07101718282D 42 46 0 0 1 0 0 0 0 0999 V2000 -4.6661 0.0901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1192 0.5105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0754 -0.0921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3450 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4790 2.5860 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 -3.5029 3.0713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 2.2377 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 -2.9680 3.0312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2771 2.4959 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 -1.5698 5.3806 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 -3.8678 2.6781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2988 1.7024 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 -2.8239 2.0754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5809 5.5297 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6658 2.5880 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 2 0 0 0 0 0 0 0 0 0 0.0425 4.7479 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3228 3.8170 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3116 3.6679 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2544 1.9971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2156 6.4606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0314 4.8969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 0.3007 3.0351 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 -1.9351 4.4498 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6770 2.7371 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 2 0 0 0 0 3 15 1 0 0 0 0 4 17 1 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 22 1 0 0 0 0 10 21 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 31 1 0 0 0 0 14 20 1 0 0 0 0 14 39 1 0 0 0 0 17 32 2 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 21 2 0 0 0 0 20 24 1 0 0 0 0 20 33 1 6 0 0 0 21 40 1 0 0 0 0 22 41 1 0 0 0 0 23 13 1 1 0 0 0 23 25 1 0 0 0 0 23 42 1 0 0 0 0 24 27 1 0 0 0 0 24 34 1 6 0 0 0 25 26 1 0 0 0 0 25 35 1 6 0 0 0 26 28 1 0 0 0 0 26 36 1 1 0 0 0 27 29 1 0 0 0 0 27 37 1 1 0 0 0 28 30 1 0 0 0 0 28 38 1 6 0 0 0 29 39 1 0 0 0 0 29 40 1 6 0 0 0 30 41 1 1 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	588.22
Volume:	569.045
LogP:	0.354
LogD:	0.484
LogS:	-4.345
# Rotatable Bonds:	5
TPSA:	195.6
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.234
Synthetic Accessibility Score:	6.292
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.16
MDCK Permeability:	2.19079101952957e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.872
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	91.2779769897461%
Volume Distribution (VD):	1.056
Pgp-substrate:	2.646576404571533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.294
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.472
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	0.888
Half-life (T1/2):	0.558

ADMET: Toxicity

hERG Blockers:	0.411
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.365
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.163
Skin Sensitization:	0.92
Carcinogencity:	0.512
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC472339

Natural Product ID:	NPC472339
*Common Name:**	IEMQJQZXAZDWFM-ZUIUKQHKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IEMQJQZXAZDWFM-ZUIUKQHKSA-N
Standard InCHI:	InChI=1S/C30H36O12/c31-13-23-25(35)26(36)28(38)30(42-23)41-22-9-6-15-3-1-2-4-17(32)8-5-16-7-10-21(19(12-16)18(22)11-15)40-29-27(37)24(34)20(33)14-39-29/h2,4,6-7,9-12,20,23-31,33-38H,1,3,5,8,13-14H2/b4-2+/t20-,23+,24-,25+,26-,27+,28+,29-,30+/m0/s1
SMILES:	C1CC2=CC(=C(C=C2)OC3C(C(C(C(O3)CO)O)O)O)C4=C(C=CC(=C4)CCC(=O)C=C1)OC5C(C(C(CO5)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359258
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003524] Meta,meta-bridged biphenyls

*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	=	12.6	%	PMID[561943]
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	18.1	%	PMID[561943]

☑ 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 NPC472339 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	369
0.1-0.2	1352
0.2-0.3	2820
0.3-0.4	6720
0.4-0.5	10367
0.5-0.6	6514
0.6-0.7	7792
0.7-0.8	6176
0.8-0.85	550
0.85-0.9	35
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8912	High Similarity	NPC474044
0.8904	High Similarity	NPC471028
0.8896	High Similarity	NPC472320
0.8873	High Similarity	NPC79957
0.88	High Similarity	NPC88886
0.88	High Similarity	NPC104172
0.8792	High Similarity	NPC116229
0.8774	High Similarity	NPC271479
0.8726	High Similarity	NPC124155
0.8726	High Similarity	NPC257566
0.8718	High Similarity	NPC47923
0.871	High Similarity	NPC308265
0.8701	High Similarity	NPC45165
0.8701	High Similarity	NPC170475
0.8699	High Similarity	NPC79908
0.8675	High Similarity	NPC107197
0.8662	High Similarity	NPC44947
0.8662	High Similarity	NPC190450
0.8662	High Similarity	NPC259834
0.8645	High Similarity	NPC156457
0.8645	High Similarity	NPC313163
0.8645	High Similarity	NPC161749
0.8645	High Similarity	NPC197896
0.8645	High Similarity	NPC258035
0.8645	High Similarity	NPC23817
0.8639	High Similarity	NPC31081
0.8639	High Similarity	NPC245219
0.8636	High Similarity	NPC26195
0.8636	High Similarity	NPC169248
0.8636	High Similarity	NPC39351
0.8636	High Similarity	NPC72649
0.8636	High Similarity	NPC97052
0.8618	High Similarity	NPC473966
0.8609	High Similarity	NPC287294
0.86	High Similarity	NPC471764
0.86	High Similarity	NPC87950
0.8599	High Similarity	NPC303913
0.859	High Similarity	NPC43761
0.859	High Similarity	NPC73511
0.8581	High Similarity	NPC473657
0.8581	High Similarity	NPC295613
0.8581	High Similarity	NPC206378
0.8571	High Similarity	NPC52598
0.8571	High Similarity	NPC80098
0.8562	High Similarity	NPC63470
0.8553	High Similarity	NPC100818
0.8553	High Similarity	NPC182350
0.8552	High Similarity	NPC166180
0.8544	High Similarity	NPC146837
0.8544	High Similarity	NPC131745
0.8544	High Similarity	NPC212099
0.8544	High Similarity	NPC101116
0.8544	High Similarity	NPC278329
0.8535	High Similarity	NPC97285
0.8535	High Similarity	NPC328093
0.8535	High Similarity	NPC246469
0.8535	High Similarity	NPC142860
0.8535	High Similarity	NPC200708
0.8535	High Similarity	NPC271270
0.8533	High Similarity	NPC291153
0.8526	High Similarity	NPC177742
0.8516	High Similarity	NPC99233
0.8509	High Similarity	NPC5319
0.8506	High Similarity	NPC121001
0.8506	High Similarity	NPC259182
0.8506	High Similarity	NPC88484
0.8506	High Similarity	NPC259767
0.8497	Intermediate Similarity	NPC213723
0.8491	Intermediate Similarity	NPC278419
0.8491	Intermediate Similarity	NPC66087
0.8491	Intermediate Similarity	NPC17432
0.8491	Intermediate Similarity	NPC183672
0.8491	Intermediate Similarity	NPC179198
0.8477	Intermediate Similarity	NPC175275
0.8471	Intermediate Similarity	NPC138811
0.8471	Intermediate Similarity	NPC473634
0.8471	Intermediate Similarity	NPC22062
0.8467	Intermediate Similarity	NPC85624
0.8466	Intermediate Similarity	NPC213052
0.8466	Intermediate Similarity	NPC168789
0.8466	Intermediate Similarity	NPC203751
0.8462	Intermediate Similarity	NPC228357
0.8457	Intermediate Similarity	NPC76047
0.8456	Intermediate Similarity	NPC469367
0.8456	Intermediate Similarity	NPC116922
0.8452	Intermediate Similarity	NPC185103
0.8452	Intermediate Similarity	NPC143851
0.8452	Intermediate Similarity	NPC210003
0.8452	Intermediate Similarity	NPC29763
0.8452	Intermediate Similarity	NPC106625
0.8452	Intermediate Similarity	NPC39360
0.8452	Intermediate Similarity	NPC83283
0.8446	Intermediate Similarity	NPC108674
0.8438	Intermediate Similarity	NPC178281
0.8438	Intermediate Similarity	NPC99216
0.8431	Intermediate Similarity	NPC158635
0.8431	Intermediate Similarity	NPC229882
0.8428	Intermediate Similarity	NPC216752
0.8428	Intermediate Similarity	NPC148273
0.8428	Intermediate Similarity	NPC472876
0.8425	Intermediate Similarity	NPC294470
0.8424	Intermediate Similarity	NPC267549
0.8421	Intermediate Similarity	NPC92054
0.8421	Intermediate Similarity	NPC4958
0.8421	Intermediate Similarity	NPC220282
0.8421	Intermediate Similarity	NPC140722
0.8418	Intermediate Similarity	NPC473623
0.8418	Intermediate Similarity	NPC153342
0.8415	Intermediate Similarity	NPC3718
0.8414	Intermediate Similarity	NPC34456
0.8411	Intermediate Similarity	NPC107120
0.8411	Intermediate Similarity	NPC74320
0.8408	Intermediate Similarity	NPC473512
0.8408	Intermediate Similarity	NPC65003
0.8408	Intermediate Similarity	NPC43638
0.8408	Intermediate Similarity	NPC129827
0.8408	Intermediate Similarity	NPC44931
0.8403	Intermediate Similarity	NPC269421
0.84	Intermediate Similarity	NPC225445
0.84	Intermediate Similarity	NPC217635
0.84	Intermediate Similarity	NPC471667
0.84	Intermediate Similarity	NPC79429
0.84	Intermediate Similarity	NPC177597
0.8397	Intermediate Similarity	NPC95090
0.8397	Intermediate Similarity	NPC470603
0.8397	Intermediate Similarity	NPC27408
0.8397	Intermediate Similarity	NPC470605
0.8397	Intermediate Similarity	NPC470604
0.8397	Intermediate Similarity	NPC477958
0.8395	Intermediate Similarity	NPC61791
0.8395	Intermediate Similarity	NPC473202
0.8395	Intermediate Similarity	NPC222455
0.8395	Intermediate Similarity	NPC246274
0.8395	Intermediate Similarity	NPC259905
0.8389	Intermediate Similarity	NPC128337
0.8389	Intermediate Similarity	NPC84207
0.8389	Intermediate Similarity	NPC49542
0.8389	Intermediate Similarity	NPC139976
0.8389	Intermediate Similarity	NPC145319
0.8389	Intermediate Similarity	NPC65833
0.8389	Intermediate Similarity	NPC5253
0.8389	Intermediate Similarity	NPC230718
0.8389	Intermediate Similarity	NPC472353
0.8387	Intermediate Similarity	NPC137813
0.8385	Intermediate Similarity	NPC178851
0.8385	Intermediate Similarity	NPC70441
0.8377	Intermediate Similarity	NPC93619
0.8377	Intermediate Similarity	NPC131874
0.8375	Intermediate Similarity	NPC121290
0.8375	Intermediate Similarity	NPC29830
0.8367	Intermediate Similarity	NPC262328
0.8367	Intermediate Similarity	NPC87777
0.8366	Intermediate Similarity	NPC111785
0.8366	Intermediate Similarity	NPC22137
0.8365	Intermediate Similarity	NPC101636
0.8364	Intermediate Similarity	NPC289876
0.8364	Intermediate Similarity	NPC475246
0.8364	Intermediate Similarity	NPC102053
0.8364	Intermediate Similarity	NPC46958
0.8364	Intermediate Similarity	NPC67629
0.8364	Intermediate Similarity	NPC79736
0.8355	Intermediate Similarity	NPC97240
0.8355	Intermediate Similarity	NPC469700
0.8355	Intermediate Similarity	NPC296377
0.8354	Intermediate Similarity	NPC241600
0.8354	Intermediate Similarity	NPC316539
0.8354	Intermediate Similarity	NPC173726
0.8354	Intermediate Similarity	NPC199357
0.8354	Intermediate Similarity	NPC208668
0.8354	Intermediate Similarity	NPC478269
0.8344	Intermediate Similarity	NPC150767
0.8344	Intermediate Similarity	NPC323593
0.8344	Intermediate Similarity	NPC265480
0.8344	Intermediate Similarity	NPC218488
0.8344	Intermediate Similarity	NPC17521
0.8344	Intermediate Similarity	NPC135370
0.8344	Intermediate Similarity	NPC149368
0.8344	Intermediate Similarity	NPC43508
0.8344	Intermediate Similarity	NPC78734
0.8344	Intermediate Similarity	NPC307938
0.8344	Intermediate Similarity	NPC127406
0.8344	Intermediate Similarity	NPC203500
0.8344	Intermediate Similarity	NPC226722
0.8344	Intermediate Similarity	NPC476301
0.8344	Intermediate Similarity	NPC261866
0.8333	Intermediate Similarity	NPC477502
0.8333	Intermediate Similarity	NPC326592
0.8333	Intermediate Similarity	NPC87304
0.8333	Intermediate Similarity	NPC268950
0.8333	Intermediate Similarity	NPC211158
0.8333	Intermediate Similarity	NPC160882
0.8333	Intermediate Similarity	NPC112701
0.8333	Intermediate Similarity	NPC78021
0.8333	Intermediate Similarity	NPC45400
0.8333	Intermediate Similarity	NPC109594
0.8333	Intermediate Similarity	NPC108706
0.8323	Intermediate Similarity	NPC475161
0.8323	Intermediate Similarity	NPC477897
0.8323	Intermediate Similarity	NPC475979
0.8323	Intermediate Similarity	NPC475366

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 NPC472339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	817
0.2-0.3	1523
0.3-0.4	2584
0.4-0.5	2141
0.5-0.6	1129
0.6-0.7	500
0.7-0.8	131
0.8-0.85	9
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9067	High Similarity	NPD8455	Phase 2
0.8645	High Similarity	NPD4381	Clinical (unspecified phase)
0.8509	High Similarity	NPD7804	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD4380	Phase 2
0.8253	Intermediate Similarity	NPD8312	Approved
0.8253	Intermediate Similarity	NPD8313	Approved
0.8242	Intermediate Similarity	NPD6559	Discontinued
0.8232	Intermediate Similarity	NPD7074	Phase 3
0.8171	Intermediate Similarity	NPD7054	Approved
0.8121	Intermediate Similarity	NPD7472	Approved
0.8101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD7075	Discontinued
0.8024	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD3818	Discontinued
0.7976	Intermediate Similarity	NPD7808	Phase 3
0.7964	Intermediate Similarity	NPD6797	Phase 2
0.7947	Intermediate Similarity	NPD7266	Discontinued
0.7908	Intermediate Similarity	NPD4628	Phase 3
0.7887	Intermediate Similarity	NPD1091	Approved
0.7875	Intermediate Similarity	NPD7819	Suspended
0.7852	Intermediate Similarity	NPD6355	Discontinued
0.7848	Intermediate Similarity	NPD7458	Discontinued
0.7843	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6674	Discontinued
0.7826	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6801	Discontinued
0.7784	Intermediate Similarity	NPD7228	Approved
0.7784	Intermediate Similarity	NPD3751	Discontinued
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6798	Discontinued
0.7765	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD3787	Discontinued
0.775	Intermediate Similarity	NPD7411	Suspended
0.7748	Intermediate Similarity	NPD7097	Phase 1
0.7738	Intermediate Similarity	NPD5844	Phase 1
0.7722	Intermediate Similarity	NPD5403	Approved
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5401	Approved
0.7677	Intermediate Similarity	NPD3750	Approved
0.7673	Intermediate Similarity	NPD1653	Approved
0.7669	Intermediate Similarity	NPD7768	Phase 2
0.7665	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6166	Phase 2
0.7665	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2424	Discontinued
0.7662	Intermediate Similarity	NPD1549	Phase 2
0.7651	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5494	Approved
0.7625	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5402	Approved
0.7602	Intermediate Similarity	NPD7240	Approved
0.76	Intermediate Similarity	NPD6233	Phase 2
0.7597	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1934	Approved
0.7593	Intermediate Similarity	NPD37	Approved
0.759	Intermediate Similarity	NPD7199	Phase 2
0.759	Intermediate Similarity	NPD6959	Discontinued
0.7582	Intermediate Similarity	NPD3748	Approved
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.758	Intermediate Similarity	NPD5058	Phase 3
0.7561	Intermediate Similarity	NPD4966	Approved
0.7561	Intermediate Similarity	NPD4965	Approved
0.7561	Intermediate Similarity	NPD4967	Phase 2
0.756	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2313	Discontinued
0.7532	Intermediate Similarity	NPD2796	Approved
0.7532	Intermediate Similarity	NPD6799	Approved
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7484	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD8651	Approved
0.747	Intermediate Similarity	NPD6234	Discontinued
0.7469	Intermediate Similarity	NPD6599	Discontinued
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7434	Intermediate Similarity	NPD1613	Approved
0.7434	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2797	Approved
0.7423	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3268	Approved
0.7403	Intermediate Similarity	NPD4538	Approved
0.7403	Intermediate Similarity	NPD4536	Approved
0.7403	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4908	Phase 1
0.7397	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3817	Phase 2
0.7386	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5124	Phase 1
0.7383	Intermediate Similarity	NPD2798	Approved
0.7372	Intermediate Similarity	NPD6005	Phase 3
0.7372	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6004	Phase 3
0.7372	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2346	Discontinued
0.7372	Intermediate Similarity	NPD6002	Phase 3
0.7372	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7584	Approved
0.7355	Intermediate Similarity	NPD5588	Approved
0.7355	Intermediate Similarity	NPD7033	Discontinued
0.7355	Intermediate Similarity	NPD5960	Phase 3
0.7355	Intermediate Similarity	NPD1510	Phase 2
0.7342	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6823	Phase 2
0.7333	Intermediate Similarity	NPD2861	Phase 2
0.7322	Intermediate Similarity	NPD6776	Approved
0.7322	Intermediate Similarity	NPD6777	Approved
0.7322	Intermediate Similarity	NPD6780	Approved
0.7322	Intermediate Similarity	NPD6779	Approved
0.7322	Intermediate Similarity	NPD6778	Approved
0.7322	Intermediate Similarity	NPD6781	Approved
0.7322	Intermediate Similarity	NPD6782	Approved
0.732	Intermediate Similarity	NPD4060	Phase 1
0.7308	Intermediate Similarity	NPD2935	Discontinued
0.7302	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7783	Phase 2
0.7301	Intermediate Similarity	NPD3226	Approved
0.7297	Intermediate Similarity	NPD7696	Phase 3
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7297	Intermediate Similarity	NPD7697	Approved
0.7297	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD8151	Discontinued
0.7285	Intermediate Similarity	NPD6832	Phase 2
0.7284	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1610	Phase 2
0.7278	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD7583	Approved
0.7273	Intermediate Similarity	NPD7157	Approved
0.7273	Intermediate Similarity	NPD1933	Approved
0.7255	Intermediate Similarity	NPD4062	Phase 3
0.7248	Intermediate Similarity	NPD3225	Approved
0.7237	Intermediate Similarity	NPD7095	Approved
0.7234	Intermediate Similarity	NPD7701	Phase 2
0.7234	Intermediate Similarity	NPD7585	Approved
0.7233	Intermediate Similarity	NPD7003	Approved
0.7229	Intermediate Similarity	NPD2801	Approved
0.7222	Intermediate Similarity	NPD6273	Approved
0.7209	Intermediate Similarity	NPD7473	Discontinued
0.7205	Intermediate Similarity	NPD1511	Approved
0.7202	Intermediate Similarity	NPD3749	Approved
0.72	Intermediate Similarity	NPD3267	Approved
0.72	Intermediate Similarity	NPD3266	Approved
0.7197	Intermediate Similarity	NPD2438	Suspended
0.7197	Intermediate Similarity	NPD4476	Approved
0.7197	Intermediate Similarity	NPD4477	Approved
0.7188	Intermediate Similarity	NPD6190	Approved
0.7183	Intermediate Similarity	NPD7843	Approved
0.7171	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7871	Phase 2
0.7166	Intermediate Similarity	NPD7870	Phase 2
0.7152	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD5126	Approved
0.7143	Intermediate Similarity	NPD5125	Phase 3
0.7135	Intermediate Similarity	NPD6232	Discontinued
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7133	Intermediate Similarity	NPD1241	Discontinued
0.7125	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1894	Discontinued
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7117	Intermediate Similarity	NPD1512	Approved
0.7117	Intermediate Similarity	NPD5049	Phase 3
0.7114	Intermediate Similarity	NPD1608	Approved
0.7107	Intermediate Similarity	NPD4534	Discontinued
0.7107	Intermediate Similarity	NPD5958	Discontinued
0.7105	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1240	Approved
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7089	Intermediate Similarity	NPD1551	Phase 2
0.7089	Intermediate Similarity	NPD6100	Approved
0.7089	Intermediate Similarity	NPD6099	Approved
0.7075	Intermediate Similarity	NPD1651	Approved
0.7073	Intermediate Similarity	NPD920	Approved
0.7073	Intermediate Similarity	NPD7427	Discontinued
0.707	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7874	Approved
0.7068	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6844	Discontinued
0.7055	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4340	Discontinued
0.7049	Intermediate Similarity	NPD6534	Approved
0.7049	Intermediate Similarity	NPD6535	Approved
0.7048	Intermediate Similarity	NPD7028	Phase 2
0.7045	Intermediate Similarity	NPD3823	Discontinued
0.7044	Intermediate Similarity	NPD2344	Approved
0.7037	Intermediate Similarity	NPD6666	Approved
0.7037	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6667	Approved
0.7031	Intermediate Similarity	NPD7801	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