NPASS Compound

Structure

NPC470780 OpenBabel07101719512D 40 45 0 0 1 0 0 0 0 0999 V2000 -1.5171 2.8603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8793 -0.0643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -1.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0916 1.5561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3150 1.9257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5914 3.2143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2468 0.9059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5028 1.9079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9038 1.5739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0814 0.8703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5771 2.2619 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2841 1.5917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3948 1.7734 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3806 0.8210 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5486 0.3571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3865 -0.1256 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2945 0.5541 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4823 0.5363 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0875 -0.6213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6625 0.2809 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8559 0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7310 0.8457 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8935 0.8881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7706 -0.5599 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2943 0.9059 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4233 3.6781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2267 2.2372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1982 0.3324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5344 -0.5953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1983 -0.7143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -1.3685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2472 -1.5131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3780 -0.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7936 1.1413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5146 -0.8015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5412 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8990 0.3818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7452 1.7980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4347 1.5573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 3 24 1 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 12 1 0 0 0 0 6 27 1 0 0 0 0 7 25 1 0 0 0 0 7 37 1 0 0 0 0 8 9 1 0 0 0 0 9 23 1 6 0 0 0 10 18 1 0 0 0 0 10 38 1 1 0 0 0 11 6 1 1 0 0 0 11 13 1 0 0 0 0 11 39 1 0 0 0 0 12 25 1 6 0 0 0 12 40 1 0 0 0 0 13 14 1 0 0 0 0 13 28 1 6 0 0 0 14 15 1 0 0 0 0 14 29 1 1 0 0 0 15 22 1 0 0 0 0 15 30 1 6 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 16 31 1 6 0 0 0 17 23 1 6 0 0 0 17 25 1 0 0 0 0 18 23 1 6 0 0 0 18 32 1 0 0 0 0 19 24 1 1 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 1 0 0 0 20 34 1 0 0 0 0 21 35 2 0 0 0 0 21 40 1 0 0 0 0 22 38 1 1 0 0 0 22 39 1 0 0 0 0 23 2 1 6 0 0 0 24 26 1 6 0 0 0 24 37 1 0 0 0 0 25 26 1 1 0 0 0 26 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.23
Volume:	524.704
LogP:	-1.093
LogD:	-0.524
LogS:	-2.726
# Rotatable Bonds:	3
TPSA:	236.06
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	7.0
Fsp3:	0.885
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:	-6.593
MDCK Permeability:	0.00017712722183205187
Pgp-inhibitor:	0.023
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.945
20% Bioavailability (F20%):	0.888
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.165
Plasma Protein Binding (PPB):	28.93620491027832%
Volume Distribution (VD):	0.343
Pgp-substrate:	45.72429275512695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.166
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.014

ADMET: Excretion

Clearance (CL):	1.099
Half-life (T1/2):	0.729

ADMET: Toxicity

hERG Blockers:	0.178
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.207
AMES Toxicity:	0.142
Rat Oral Acute Toxicity:	0.211
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.117
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC470780

Natural Product ID:	NPC470780
*Common Name:**	Yadanzigan
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GLBAPTKVDVXEGQ-DCGYBIAKSA-N
Standard InCHI:	InChI=1S/C26H38O14/c1-8-4-10(38-22-15(30)14(29)13(28)11(6-27)39-22)18(32)23(2)9(8)5-12-25-7-37-24(3,19(33)16(31)17(23)25)26(25,36)20(34)21(35)40-12/h4,9-20,22,27-34,36H,5-7H2,1-3H3/t9-,10-,11+,12+,13+,14-,15+,16+,17+,18+,19-,20-,22+,23-,24-,25+,26+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2C=C(C)[C@H]3[C@@]([C@@H]2O)(C)[C@H]2[C@@H](O)[C@H](O)[C@]4([C@]5([C@@]2([C@@H](C3)OC(=O)[C@@H]5O)CO4)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2228451
PubChem CID:	76307878
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14948	Brucea javanica	Species	Simaroubaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.6	%	PMID[536277]

☑ 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 NPC470780 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	292
0.1-0.2	1701
0.2-0.3	4593
0.3-0.4	7608
0.4-0.5	11511
0.5-0.6	8269
0.6-0.7	4903
0.7-0.8	2700
0.8-0.85	760
0.85-0.9	321
0.9-0.95	38
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC122971
0.9127	High Similarity	NPC596
0.912	High Similarity	NPC262813
0.9113	High Similarity	NPC478151
0.9106	High Similarity	NPC478065
0.9106	High Similarity	NPC478064
0.9106	High Similarity	NPC475377
0.9106	High Similarity	NPC262796
0.9106	High Similarity	NPC172374
0.9106	High Similarity	NPC475167
0.9106	High Similarity	NPC476074
0.9106	High Similarity	NPC134914
0.9106	High Similarity	NPC173435
0.9106	High Similarity	NPC329993
0.9106	High Similarity	NPC264566
0.9106	High Similarity	NPC301639
0.9106	High Similarity	NPC45346
0.906	High Similarity	NPC473590
0.906	High Similarity	NPC176513
0.906	High Similarity	NPC470775
0.9048	High Similarity	NPC141215
0.9048	High Similarity	NPC471089
0.9048	High Similarity	NPC190065
0.9048	High Similarity	NPC251998
0.9032	High Similarity	NPC478152
0.9032	High Similarity	NPC478154
0.9032	High Similarity	NPC478153
0.9032	High Similarity	NPC478150
0.8976	High Similarity	NPC295885
0.8976	High Similarity	NPC140045
0.8952	High Similarity	NPC25998
0.8952	High Similarity	NPC477197
0.8952	High Similarity	NPC478155
0.8943	High Similarity	NPC477078
0.8943	High Similarity	NPC329923
0.8943	High Similarity	NPC475281
0.8943	High Similarity	NPC470476
0.8943	High Similarity	NPC477075
0.8943	High Similarity	NPC470475
0.8926	High Similarity	NPC478066
0.8926	High Similarity	NPC67251
0.8917	High Similarity	NPC75417
0.8871	High Similarity	NPC470912
0.8871	High Similarity	NPC477077
0.8871	High Similarity	NPC470913
0.8871	High Similarity	NPC477196
0.8871	High Similarity	NPC477076
0.8871	High Similarity	NPC477079
0.8852	High Similarity	NPC470477
0.8852	High Similarity	NPC470922
0.8843	High Similarity	NPC40775
0.8843	High Similarity	NPC107966
0.8843	High Similarity	NPC249848
0.8843	High Similarity	NPC235438
0.8833	High Similarity	NPC112038
0.8824	High Similarity	NPC470776
0.8824	High Similarity	NPC188667
0.8824	High Similarity	NPC204552
0.8814	High Similarity	NPC259306
0.8814	High Similarity	NPC470628
0.8814	High Similarity	NPC474046
0.8814	High Similarity	NPC474734
0.879	High Similarity	NPC477194
0.879	High Similarity	NPC477193
0.879	High Similarity	NPC477192
0.879	High Similarity	NPC477191
0.877	High Similarity	NPC30735
0.877	High Similarity	NPC281148
0.877	High Similarity	NPC91693
0.877	High Similarity	NPC265557
0.877	High Similarity	NPC18945
0.877	High Similarity	NPC235405
0.877	High Similarity	NPC105926
0.876	High Similarity	NPC477046
0.876	High Similarity	NPC102822
0.876	High Similarity	NPC79250
0.876	High Similarity	NPC290746
0.875	High Similarity	NPC157868
0.875	High Similarity	NPC469945
0.875	High Similarity	NPC114441
0.875	High Similarity	NPC6377
0.875	High Similarity	NPC472949
0.875	High Similarity	NPC475775
0.875	High Similarity	NPC309780
0.875	High Similarity	NPC475171
0.875	High Similarity	NPC214484
0.875	High Similarity	NPC35405
0.875	High Similarity	NPC180550
0.875	High Similarity	NPC11551
0.875	High Similarity	NPC473884
0.875	High Similarity	NPC39211
0.875	High Similarity	NPC208381
0.875	High Similarity	NPC476529
0.8739	High Similarity	NPC474654
0.8739	High Similarity	NPC309433
0.8739	High Similarity	NPC470854
0.8739	High Similarity	NPC97908
0.8739	High Similarity	NPC287343
0.8739	High Similarity	NPC122033
0.873	High Similarity	NPC473918
0.873	High Similarity	NPC192765
0.873	High Similarity	NPC277212
0.873	High Similarity	NPC477195
0.873	High Similarity	NPC71391
0.873	High Similarity	NPC476776
0.873	High Similarity	NPC30279
0.873	High Similarity	NPC178264
0.873	High Similarity	NPC46823
0.8729	High Similarity	NPC469877
0.8729	High Similarity	NPC470919
0.872	High Similarity	NPC141600
0.872	High Similarity	NPC11577
0.872	High Similarity	NPC82380
0.872	High Similarity	NPC252289
0.872	High Similarity	NPC88311
0.872	High Similarity	NPC9470
0.872	High Similarity	NPC115656
0.872	High Similarity	NPC273878
0.872	High Similarity	NPC97918
0.872	High Similarity	NPC107536
0.872	High Similarity	NPC244296
0.872	High Similarity	NPC280029
0.872	High Similarity	NPC472267
0.872	High Similarity	NPC305793
0.872	High Similarity	NPC269484
0.872	High Similarity	NPC1314
0.872	High Similarity	NPC252657
0.872	High Similarity	NPC470518
0.8718	High Similarity	NPC302146
0.8699	High Similarity	NPC24651
0.8699	High Similarity	NPC476729
0.8699	High Similarity	NPC23275
0.8689	High Similarity	NPC213952
0.8689	High Similarity	NPC312833
0.8678	High Similarity	NPC473645
0.8678	High Similarity	NPC109607
0.8678	High Similarity	NPC473130
0.8678	High Similarity	NPC107338
0.8667	High Similarity	NPC251310
0.8667	High Similarity	NPC286347
0.8667	High Similarity	NPC297179
0.8661	High Similarity	NPC225791
0.8651	High Similarity	NPC271610
0.8651	High Similarity	NPC476775
0.8651	High Similarity	NPC476780
0.8651	High Similarity	NPC476774
0.8644	High Similarity	NPC311592
0.8644	High Similarity	NPC75167
0.864	High Similarity	NPC475636
0.864	High Similarity	NPC295220
0.8629	High Similarity	NPC181066
0.8629	High Similarity	NPC285091
0.8629	High Similarity	NPC87662
0.8629	High Similarity	NPC469947
0.8629	High Similarity	NPC470218
0.8618	High Similarity	NPC257211
0.8618	High Similarity	NPC227397
0.8607	High Similarity	NPC222580
0.8607	High Similarity	NPC31193
0.8607	High Similarity	NPC31838
0.8607	High Similarity	NPC62725
0.8607	High Similarity	NPC223301
0.8607	High Similarity	NPC242840
0.8607	High Similarity	NPC86222
0.8607	High Similarity	NPC159309
0.8607	High Similarity	NPC11242
0.8607	High Similarity	NPC171544
0.8607	High Similarity	NPC297263
0.8607	High Similarity	NPC22956
0.8607	High Similarity	NPC476204
0.8607	High Similarity	NPC104372
0.8607	High Similarity	NPC301449
0.8607	High Similarity	NPC470779
0.8607	High Similarity	NPC114484
0.8607	High Similarity	NPC64715
0.8607	High Similarity	NPC170084
0.8595	High Similarity	NPC477071
0.8595	High Similarity	NPC469488
0.8594	High Similarity	NPC476778
0.8594	High Similarity	NPC476777
0.8583	High Similarity	NPC312650
0.8583	High Similarity	NPC471855
0.8583	High Similarity	NPC224121
0.8583	High Similarity	NPC473519
0.8583	High Similarity	NPC473805
0.8583	High Similarity	NPC473968
0.8583	High Similarity	NPC473405
0.8583	High Similarity	NPC474483
0.8571	High Similarity	NPC265841
0.8571	High Similarity	NPC54614
0.8571	High Similarity	NPC309096
0.8571	High Similarity	NPC47995
0.8571	High Similarity	NPC476966
0.8571	High Similarity	NPC181145
0.8571	High Similarity	NPC475633
0.8548	High Similarity	NPC33068
0.8548	High Similarity	NPC130229
0.8537	High Similarity	NPC471965
0.8537	High Similarity	NPC236870
0.8537	High Similarity	NPC10607

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 NPC470780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	1880
0.2-0.3	3752
0.3-0.4	2072
0.4-0.5	649
0.5-0.6	340
0.6-0.7	148
0.7-0.8	48
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8583	High Similarity	NPD8295	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD8328	Phase 3
0.8455	Intermediate Similarity	NPD8516	Approved
0.8455	Intermediate Similarity	NPD8517	Approved
0.8455	Intermediate Similarity	NPD8515	Approved
0.8455	Intermediate Similarity	NPD8513	Phase 3
0.8281	Intermediate Similarity	NPD7319	Approved
0.822	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7507	Approved
0.8	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6686	Approved
0.7886	Intermediate Similarity	NPD8133	Approved
0.7857	Intermediate Similarity	NPD7516	Approved
0.7786	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD7327	Approved
0.7778	Intermediate Similarity	NPD7328	Approved
0.7734	Intermediate Similarity	NPD8380	Approved
0.7734	Intermediate Similarity	NPD8335	Approved
0.7734	Intermediate Similarity	NPD8378	Approved
0.7734	Intermediate Similarity	NPD8379	Approved
0.7734	Intermediate Similarity	NPD8033	Approved
0.7734	Intermediate Similarity	NPD8296	Approved
0.7724	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD8293	Discontinued
0.7674	Intermediate Similarity	NPD6370	Approved
0.7656	Intermediate Similarity	NPD8294	Approved
0.7656	Intermediate Similarity	NPD8377	Approved
0.7597	Intermediate Similarity	NPD6921	Approved
0.7576	Intermediate Similarity	NPD8074	Phase 3
0.7561	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7492	Approved
0.7519	Intermediate Similarity	NPD6059	Approved
0.7519	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6616	Approved
0.7462	Intermediate Similarity	NPD7503	Approved
0.7444	Intermediate Similarity	NPD7078	Approved
0.7422	Intermediate Similarity	NPD7115	Discovery
0.7398	Intermediate Similarity	NPD6412	Phase 2
0.7385	Intermediate Similarity	NPD6319	Approved
0.7328	Intermediate Similarity	NPD6016	Approved
0.7328	Intermediate Similarity	NPD6015	Approved
0.7273	Intermediate Similarity	NPD5988	Approved
0.7258	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4225	Approved
0.7244	Intermediate Similarity	NPD6882	Approved
0.7154	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7109	Intermediate Similarity	NPD8297	Approved
0.7054	Intermediate Similarity	NPD4632	Approved
0.704	Intermediate Similarity	NPD6402	Approved
0.704	Intermediate Similarity	NPD5739	Approved
0.704	Intermediate Similarity	NPD6675	Approved
0.704	Intermediate Similarity	NPD7128	Approved
0.7031	Intermediate Similarity	NPD6650	Approved
0.7031	Intermediate Similarity	NPD6649	Approved
0.7007	Intermediate Similarity	NPD6033	Approved
0.6967	Remote Similarity	NPD7638	Approved
0.6929	Remote Similarity	NPD7320	Approved
0.6929	Remote Similarity	NPD6881	Approved
0.6929	Remote Similarity	NPD6899	Approved
0.6911	Remote Similarity	NPD7640	Approved
0.6911	Remote Similarity	NPD7639	Approved
0.685	Remote Similarity	NPD5697	Approved
0.685	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5701	Approved
0.6825	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4634	Approved
0.6822	Remote Similarity	NPD7290	Approved
0.6822	Remote Similarity	NPD6883	Approved
0.6822	Remote Similarity	NPD7102	Approved
0.6772	Remote Similarity	NPD6008	Approved
0.6769	Remote Similarity	NPD6869	Approved
0.6769	Remote Similarity	NPD6847	Approved
0.6769	Remote Similarity	NPD8130	Phase 1
0.6769	Remote Similarity	NPD6617	Approved
0.675	Remote Similarity	NPD6411	Approved
0.6748	Remote Similarity	NPD7902	Approved
0.6744	Remote Similarity	NPD6013	Approved
0.6744	Remote Similarity	NPD6012	Approved
0.6744	Remote Similarity	NPD6014	Approved
0.6739	Remote Similarity	NPD8451	Approved
0.672	Remote Similarity	NPD5344	Discontinued
0.6715	Remote Similarity	NPD7604	Phase 2
0.6694	Remote Similarity	NPD5779	Approved
0.6694	Remote Similarity	NPD6399	Phase 3
0.6694	Remote Similarity	NPD5778	Approved
0.6691	Remote Similarity	NPD5983	Phase 2
0.6691	Remote Similarity	NPD8448	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD8392	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD8391	Approved
0.6667	Remote Similarity	NPD8390	Approved
0.6641	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7748	Approved
0.6621	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7260	Phase 2
0.6619	Remote Similarity	NPD6336	Discontinued
0.6613	Remote Similarity	NPD4755	Approved
0.6612	Remote Similarity	NPD7983	Approved
0.6612	Remote Similarity	NPD7515	Phase 2
0.6594	Remote Similarity	NPD6067	Discontinued
0.6591	Remote Similarity	NPD6053	Discontinued
0.6583	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6101	Approved
0.6565	Remote Similarity	NPD6371	Approved
0.656	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD8299	Approved
0.6547	Remote Similarity	NPD8340	Approved
0.6547	Remote Similarity	NPD8342	Approved
0.6547	Remote Similarity	NPD8341	Approved
0.6545	Remote Similarity	NPD7799	Discontinued
0.6535	Remote Similarity	NPD5211	Phase 2
0.6508	Remote Similarity	NPD5286	Approved
0.6508	Remote Similarity	NPD4700	Approved
0.6508	Remote Similarity	NPD4696	Approved
0.6508	Remote Similarity	NPD5285	Approved
0.6504	Remote Similarity	NPD7900	Approved
0.6504	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD8415	Approved
0.648	Remote Similarity	NPD6083	Phase 2
0.648	Remote Similarity	NPD6084	Phase 2
0.6475	Remote Similarity	NPD7829	Approved
0.6475	Remote Similarity	NPD7830	Approved
0.6471	Remote Similarity	NPD8407	Phase 2
0.6458	Remote Similarity	NPD6845	Suspended
0.6449	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7625	Phase 1
0.6444	Remote Similarity	NPD6274	Approved
0.6434	Remote Similarity	NPD5141	Approved
0.6423	Remote Similarity	NPD7101	Approved
0.6423	Remote Similarity	NPD7100	Approved
0.6407	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5224	Approved
0.6406	Remote Similarity	NPD4633	Approved
0.6406	Remote Similarity	NPD5225	Approved
0.6406	Remote Similarity	NPD7632	Discontinued
0.6406	Remote Similarity	NPD5226	Approved
0.6403	Remote Similarity	NPD8080	Discontinued
0.64	Remote Similarity	NPD4697	Phase 3
0.6397	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD8368	Discontinued
0.6385	Remote Similarity	NPD4767	Approved
0.6385	Remote Similarity	NPD4768	Approved
0.6378	Remote Similarity	NPD6648	Approved
0.6371	Remote Similarity	NPD5282	Discontinued
0.6357	Remote Similarity	NPD5174	Approved
0.6357	Remote Similarity	NPD7642	Approved
0.6357	Remote Similarity	NPD5175	Approved
0.635	Remote Similarity	NPD6335	Approved
0.6341	Remote Similarity	NPD7637	Suspended
0.6341	Remote Similarity	NPD8034	Phase 2
0.6341	Remote Similarity	NPD8035	Phase 2
0.6331	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD6908	Approved
0.6331	Remote Similarity	NPD8444	Approved
0.6331	Remote Similarity	NPD6909	Approved
0.6328	Remote Similarity	NPD1700	Approved
0.6328	Remote Similarity	NPD5223	Approved
0.632	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD5956	Approved
0.6311	Remote Similarity	NPD5328	Approved
0.6299	Remote Similarity	NPD5696	Approved
0.6288	Remote Similarity	NPD4729	Approved
0.6288	Remote Similarity	NPD4730	Approved
0.6281	Remote Similarity	NPD3573	Approved
0.6277	Remote Similarity	NPD6317	Approved
0.627	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5222	Approved
0.627	Remote Similarity	NPD5221	Approved
0.627	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD7228	Approved
0.6233	Remote Similarity	NPD8338	Approved
0.6232	Remote Similarity	NPD6314	Approved
0.6232	Remote Similarity	NPD6313	Approved
0.6231	Remote Similarity	NPD4754	Approved
0.622	Remote Similarity	NPD5173	Approved
0.621	Remote Similarity	NPD6079	Approved
0.6204	Remote Similarity	NPD6868	Approved
0.6198	Remote Similarity	NPD3618	Phase 1
0.6194	Remote Similarity	NPD5248	Approved
0.6194	Remote Similarity	NPD5249	Phase 3
0.6194	Remote Similarity	NPD5251	Approved
0.6194	Remote Similarity	NPD5247	Approved
0.6194	Remote Similarity	NPD5250	Approved
0.619	Remote Similarity	NPD5695	Phase 3
0.6167	Remote Similarity	NPD4786	Approved
0.6165	Remote Similarity	NPD5128	Approved
0.616	Remote Similarity	NPD8171	Discontinued
0.6148	Remote Similarity	NPD7524	Approved
0.6136	Remote Similarity	NPD8360	Approved
0.6136	Remote Similarity	NPD8435	Approved
0.6136	Remote Similarity	NPD8361	Approved
0.6134	Remote Similarity	NPD3667	Approved
0.6122	Remote Similarity	NPD8449	Approved
0.6116	Remote Similarity	NPD7520	Clinical (unspecified phase)

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