NPASS Compound

Structure

NPC474000 OpenBabel07101719132D 32 33 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 0.8660 -0.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 3 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 0.0000 -0.0000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 14 2 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 20 2 0 0 0 0 12 18 1 0 0 0 0 12 26 2 0 0 0 0 13 21 1 0 0 0 0 13 32 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 20 32 1 0 0 0 0 21 25 1 0 0 0 0 21 28 1 0 0 0 0 22 24 1 0 0 0 0 23 29 1 0 0 0 0 24 30 2 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.2
Volume:	461.647
LogP:	4.572
LogD:	2.972
LogS:	-3.907
# Rotatable Bonds:	9
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	3.583
Fsp3:	0.36
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.897
MDCK Permeability:	9.958386726793833e-06
Pgp-inhibitor:	0.134
Pgp-substrate:	0.68
Human Intestinal Absorption (HIA):	0.279
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.389

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	99.96379852294922%
Volume Distribution (VD):	0.561
Pgp-substrate:	1.3054990768432617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.56
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.672
CYP2C9-substrate:	0.473
CYP2D6-inhibitor:	0.755
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.416
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	11.043
Half-life (T1/2):	0.249

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.242
AMES Toxicity:	0.75
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.642
Skin Sensitization:	0.158
Carcinogencity:	0.239
Eye Corrosion:	0.003
Eye Irritation:	0.168
Respiratory Toxicity:	0.227

Download Data

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

Natural Product: NPC474000

Natural Product ID:	NPC474000
*Common Name:**	Tenellone A
IUPAC Name:	2-[3-(2,3-dihydroxy-3-methylbutoxy)-2-hydroxy-5-methylbenzoyl]-6-hydroxy-3-(3-methylbut-2-enyl)benzaldehyde
Synonyms:
Standard InCHIKey:	AXMCRMUBMNEKLN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H30O7/c1-14(2)6-7-16-8-9-19(27)18(12-26)22(16)24(30)17-10-15(3)11-20(23(17)29)32-13-21(28)25(4,5)31/h6,8-12,21,27-29,31H,7,13H2,1-5H3
SMILES:	CC1=CC(=C(C(=C1)OCC(C(C)(C)O)O)O)C(=O)C2=C(C=CC(=C2C=O)O)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457810
PubChem CID:	44583991
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO33124	Diaporthe	Genus	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844962]

☑ 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
IC50	2

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6488	Individual Protein	cGMP-dependent protein kinase	Eimeria tenella	IC50	=	12600.0	nM	PMID[498392]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	IC50	=	1800.0	nM	PMID[498392]

☑ 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 NPC474000 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	385
0.1-0.2	1538
0.2-0.3	3758
0.3-0.4	9640
0.4-0.5	8757
0.5-0.6	3438
0.6-0.7	5929
0.7-0.8	7788
0.8-0.85	1290
0.85-0.9	172
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.973	High Similarity	NPC475770
0.902	High Similarity	NPC164912
0.8954	High Similarity	NPC118427
0.8917	High Similarity	NPC472902
0.8903	High Similarity	NPC300757
0.8903	High Similarity	NPC180901
0.8831	High Similarity	NPC144283
0.8808	High Similarity	NPC160777
0.8808	High Similarity	NPC73416
0.8805	High Similarity	NPC472964
0.8797	High Similarity	NPC36217
0.8797	High Similarity	NPC472962
0.8797	High Similarity	NPC472961
0.879	High Similarity	NPC136674
0.8774	High Similarity	NPC131121
0.8774	High Similarity	NPC137125
0.8774	High Similarity	NPC3744
0.875	High Similarity	NPC124038
0.875	High Similarity	NPC186686
0.875	High Similarity	NPC39361
0.8726	High Similarity	NPC472455
0.8726	High Similarity	NPC279605
0.8718	High Similarity	NPC472905
0.871	High Similarity	NPC75377
0.871	High Similarity	NPC302783
0.871	High Similarity	NPC473201
0.871	High Similarity	NPC70320
0.8704	High Similarity	NPC117854
0.8704	High Similarity	NPC6588
0.8704	High Similarity	NPC186392
0.8704	High Similarity	NPC477154
0.8696	High Similarity	NPC293319
0.8696	High Similarity	NPC303174
0.8688	High Similarity	NPC474033
0.8688	High Similarity	NPC474034
0.8688	High Similarity	NPC201800
0.8684	High Similarity	NPC478019
0.8684	High Similarity	NPC287495
0.8684	High Similarity	NPC9370
0.8679	High Similarity	NPC321399
0.8679	High Similarity	NPC471973
0.8679	High Similarity	NPC474960
0.8671	High Similarity	NPC474055
0.8671	High Similarity	NPC472963
0.8671	High Similarity	NPC291508
0.8671	High Similarity	NPC27337
0.8671	High Similarity	NPC472598
0.8667	High Similarity	NPC84273
0.8662	High Similarity	NPC117992
0.8662	High Similarity	NPC256925
0.8662	High Similarity	NPC57674
0.8662	High Similarity	NPC168247
0.8662	High Similarity	NPC234255
0.8662	High Similarity	NPC152951
0.8662	High Similarity	NPC230149
0.8662	High Similarity	NPC472280
0.8654	High Similarity	NPC237994
0.8642	High Similarity	NPC170245
0.8642	High Similarity	NPC43319
0.8634	High Similarity	NPC147596
0.8634	High Similarity	NPC7483
0.8634	High Similarity	NPC477689
0.8625	High Similarity	NPC474038
0.8625	High Similarity	NPC472632
0.8625	High Similarity	NPC472634
0.8625	High Similarity	NPC61010
0.8625	High Similarity	NPC134783
0.8618	High Similarity	NPC300603
0.8618	High Similarity	NPC91694
0.8616	High Similarity	NPC74178
0.8616	High Similarity	NPC235448
0.8616	High Similarity	NPC204879
0.8616	High Similarity	NPC184755
0.8616	High Similarity	NPC210459
0.8608	High Similarity	NPC35038
0.8608	High Similarity	NPC213401
0.8608	High Similarity	NPC478223
0.8608	High Similarity	NPC472907
0.8608	High Similarity	NPC278778
0.8608	High Similarity	NPC195796
0.8608	High Similarity	NPC291878
0.8608	High Similarity	NPC24640
0.8606	High Similarity	NPC199357
0.86	High Similarity	NPC78987
0.86	High Similarity	NPC82336
0.8599	High Similarity	NPC33051
0.8599	High Similarity	NPC227337
0.8599	High Similarity	NPC70433
0.8599	High Similarity	NPC273462
0.8599	High Similarity	NPC49402
0.8589	High Similarity	NPC218226
0.8589	High Similarity	NPC474024
0.858	High Similarity	NPC62261
0.858	High Similarity	NPC239752
0.858	High Similarity	NPC326520
0.858	High Similarity	NPC108433
0.858	High Similarity	NPC472450
0.858	High Similarity	NPC300053
0.858	High Similarity	NPC475888
0.858	High Similarity	NPC472277
0.858	High Similarity	NPC275780
0.8571	High Similarity	NPC211107
0.8571	High Similarity	NPC61594
0.8571	High Similarity	NPC472635
0.8571	High Similarity	NPC474162
0.8571	High Similarity	NPC476247
0.8571	High Similarity	NPC56735
0.8571	High Similarity	NPC474150
0.8562	High Similarity	NPC282009
0.8562	High Similarity	NPC174953
0.8562	High Similarity	NPC472624
0.8562	High Similarity	NPC228785
0.8562	High Similarity	NPC119209
0.8562	High Similarity	NPC192686
0.8562	High Similarity	NPC472631
0.8562	High Similarity	NPC56085
0.8562	High Similarity	NPC118256
0.8562	High Similarity	NPC287328
0.8562	High Similarity	NPC472630
0.8562	High Similarity	NPC475784
0.8562	High Similarity	NPC476980
0.8562	High Similarity	NPC14353
0.8562	High Similarity	NPC328102
0.8562	High Similarity	NPC299436
0.8553	High Similarity	NPC199463
0.8553	High Similarity	NPC187745
0.8553	High Similarity	NPC161960
0.8553	High Similarity	NPC218313
0.8553	High Similarity	NPC474681
0.8553	High Similarity	NPC239608
0.8553	High Similarity	NPC219867
0.8553	High Similarity	NPC299520
0.8553	High Similarity	NPC78071
0.8553	High Similarity	NPC178976
0.8553	High Similarity	NPC52889
0.8553	High Similarity	NPC180011
0.8553	High Similarity	NPC46161
0.8553	High Similarity	NPC129684
0.8553	High Similarity	NPC304008
0.8553	High Similarity	NPC37543
0.8544	High Similarity	NPC470327
0.8544	High Similarity	NPC45849
0.8544	High Similarity	NPC200761
0.8544	High Similarity	NPC321779
0.8544	High Similarity	NPC67396
0.8544	High Similarity	NPC477503
0.8537	High Similarity	NPC288813
0.8535	High Similarity	NPC199773
0.8535	High Similarity	NPC149889
0.8535	High Similarity	NPC180388
0.8535	High Similarity	NPC257648
0.8535	High Similarity	NPC312338
0.8535	High Similarity	NPC477231
0.8528	High Similarity	NPC477517
0.8528	High Similarity	NPC235610
0.8528	High Similarity	NPC263212
0.8528	High Similarity	NPC39091
0.8528	High Similarity	NPC119589
0.8526	High Similarity	NPC472279
0.8519	High Similarity	NPC475985
0.8519	High Similarity	NPC474240
0.8519	High Similarity	NPC189473
0.8519	High Similarity	NPC152659
0.8519	High Similarity	NPC248638
0.8519	High Similarity	NPC23298
0.8519	High Similarity	NPC220313
0.8519	High Similarity	NPC472625
0.8519	High Similarity	NPC205265
0.8519	High Similarity	NPC236521
0.8519	High Similarity	NPC472281
0.8519	High Similarity	NPC18100
0.8509	High Similarity	NPC40491
0.8509	High Similarity	NPC472906
0.8509	High Similarity	NPC349525
0.8509	High Similarity	NPC278052
0.8509	High Similarity	NPC471210
0.8509	High Similarity	NPC474187
0.8509	High Similarity	NPC474186
0.8509	High Similarity	NPC478222
0.8509	High Similarity	NPC57715
0.8509	High Similarity	NPC26326
0.8509	High Similarity	NPC471499
0.8509	High Similarity	NPC234644
0.85	High Similarity	NPC100123
0.85	High Similarity	NPC476242
0.85	High Similarity	NPC250214
0.85	High Similarity	NPC474290
0.85	High Similarity	NPC329091
0.85	High Similarity	NPC85121
0.85	High Similarity	NPC187792
0.85	High Similarity	NPC95936
0.85	High Similarity	NPC477410
0.85	High Similarity	NPC473990
0.85	High Similarity	NPC22192
0.85	High Similarity	NPC55738
0.8497	Intermediate Similarity	NPC275278
0.8491	Intermediate Similarity	NPC282307
0.8491	Intermediate Similarity	NPC170026
0.8491	Intermediate Similarity	NPC6633
0.8491	Intermediate Similarity	NPC5379

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 NPC474000 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	957
0.2-0.3	1625
0.3-0.4	2577
0.4-0.5	1850
0.5-0.6	1045
0.6-0.7	586
0.7-0.8	159
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8481	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD1934	Approved
0.8375	Intermediate Similarity	NPD3882	Suspended
0.825	Intermediate Similarity	NPD2801	Approved
0.8144	Intermediate Similarity	NPD3818	Discontinued
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.8092	Intermediate Similarity	NPD2799	Discontinued
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD5494	Approved
0.7987	Intermediate Similarity	NPD2346	Discontinued
0.7976	Intermediate Similarity	NPD7473	Discontinued
0.7973	Intermediate Similarity	NPD9494	Approved
0.795	Intermediate Similarity	NPD4380	Phase 2
0.7941	Intermediate Similarity	NPD7074	Phase 3
0.7914	Intermediate Similarity	NPD7819	Suspended
0.7911	Intermediate Similarity	NPD1511	Approved
0.7895	Intermediate Similarity	NPD447	Suspended
0.7882	Intermediate Similarity	NPD7054	Approved
0.7882	Intermediate Similarity	NPD5844	Phase 1
0.7879	Intermediate Similarity	NPD7075	Discontinued
0.7871	Intermediate Similarity	NPD2344	Approved
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7841	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7472	Approved
0.7823	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1512	Approved
0.7805	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3226	Approved
0.7758	Intermediate Similarity	NPD3817	Phase 2
0.775	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6801	Discontinued
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7712	Intermediate Similarity	NPD4060	Phase 1
0.7707	Intermediate Similarity	NPD1549	Phase 2
0.7701	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2313	Discontinued
0.7688	Intermediate Similarity	NPD6797	Phase 2
0.7673	Intermediate Similarity	NPD2309	Approved
0.7669	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD8313	Approved
0.7657	Intermediate Similarity	NPD8312	Approved
0.7651	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7251	Discontinued
0.7643	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD1247	Approved
0.7633	Intermediate Similarity	NPD6959	Discontinued
0.7619	Intermediate Similarity	NPD919	Approved
0.76	Intermediate Similarity	NPD7808	Phase 3
0.7597	Intermediate Similarity	NPD943	Approved
0.759	Intermediate Similarity	NPD1465	Phase 2
0.758	Intermediate Similarity	NPD2796	Approved
0.7578	Intermediate Similarity	NPD6799	Approved
0.7568	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1933	Approved
0.7547	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5402	Approved
0.7544	Intermediate Similarity	NPD3926	Phase 2
0.7528	Intermediate Similarity	NPD8434	Phase 2
0.7516	Intermediate Similarity	NPD1510	Phase 2
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7486	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6273	Approved
0.7484	Intermediate Similarity	NPD2424	Discontinued
0.7484	Intermediate Similarity	NPD1240	Approved
0.7483	Intermediate Similarity	NPD1470	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7411	Suspended
0.7468	Intermediate Similarity	NPD1551	Phase 2
0.7459	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2649	Approved
0.7455	Intermediate Similarity	NPD2651	Approved
0.7451	Intermediate Similarity	NPD6832	Phase 2
0.7439	Intermediate Similarity	NPD5403	Approved
0.7436	Intermediate Similarity	NPD6355	Discontinued
0.7434	Intermediate Similarity	NPD2798	Approved
0.7423	Intermediate Similarity	NPD4662	Approved
0.7423	Intermediate Similarity	NPD4661	Approved
0.7423	Intermediate Similarity	NPD2532	Approved
0.7423	Intermediate Similarity	NPD2534	Approved
0.7423	Intermediate Similarity	NPD2533	Approved
0.7421	Intermediate Similarity	NPD1471	Phase 3
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.7405	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3027	Phase 3
0.7389	Intermediate Similarity	NPD1607	Approved
0.7375	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD6798	Discontinued
0.7353	Intermediate Similarity	NPD3749	Approved
0.7347	Intermediate Similarity	NPD5536	Phase 2
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD37	Approved
0.7321	Intermediate Similarity	NPD6844	Discontinued
0.7317	Intermediate Similarity	NPD5401	Approved
0.7303	Intermediate Similarity	NPD1876	Approved
0.7299	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD4966	Approved
0.7294	Intermediate Similarity	NPD4965	Approved
0.7285	Intermediate Similarity	NPD9717	Approved
0.7284	Intermediate Similarity	NPD4110	Phase 3
0.7284	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD8166	Discontinued
0.7284	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7003	Approved
0.7279	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6778	Approved
0.7273	Intermediate Similarity	NPD6779	Approved
0.7273	Intermediate Similarity	NPD6780	Approved
0.7273	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD6781	Approved
0.7273	Intermediate Similarity	NPD6776	Approved
0.7273	Intermediate Similarity	NPD5049	Phase 3
0.7273	Intermediate Similarity	NPD6777	Approved
0.7261	Intermediate Similarity	NPD3620	Phase 2
0.7261	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4477	Approved
0.725	Intermediate Similarity	NPD2438	Suspended
0.725	Intermediate Similarity	NPD4476	Approved
0.7248	Intermediate Similarity	NPD1651	Approved
0.7247	Intermediate Similarity	NPD7685	Pre-registration
0.7246	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD6190	Approved
0.7238	Intermediate Similarity	NPD8150	Discontinued
0.7229	Intermediate Similarity	NPD920	Approved
0.7225	Intermediate Similarity	NPD8127	Discontinued
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7222	Intermediate Similarity	NPD2800	Approved
0.7219	Intermediate Similarity	NPD1201	Approved
0.7216	Intermediate Similarity	NPD7228	Approved
0.7191	Intermediate Similarity	NPD5953	Discontinued
0.719	Intermediate Similarity	NPD1283	Approved
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7188	Intermediate Similarity	NPD3748	Approved
0.7184	Intermediate Similarity	NPD3787	Discontinued
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD3455	Phase 2
0.7143	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD5404	Approved
0.7135	Intermediate Similarity	NPD2296	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD411	Approved
0.7134	Intermediate Similarity	NPD3764	Approved
0.7124	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6674	Discontinued
0.7117	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD230	Phase 1
0.7105	Intermediate Similarity	NPD6823	Phase 2
0.7097	Intermediate Similarity	NPD5647	Approved
0.7095	Intermediate Similarity	NPD3823	Discontinued
0.7091	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6233	Phase 2
0.7086	Intermediate Similarity	NPD4626	Approved
0.7081	Intermediate Similarity	NPD7033	Discontinued
0.7076	Intermediate Similarity	NPD5761	Phase 2
0.7076	Intermediate Similarity	NPD5760	Phase 2
0.7075	Intermediate Similarity	NPD5283	Phase 1
0.7075	Intermediate Similarity	NPD1241	Discontinued
0.707	Intermediate Similarity	NPD7095	Approved
0.7068	Intermediate Similarity	NPD7697	Approved
0.7068	Intermediate Similarity	NPD7696	Phase 3
0.7068	Intermediate Similarity	NPD7698	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7055	Intermediate Similarity	NPD228	Approved
0.7051	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2979	Phase 3
0.7032	Intermediate Similarity	NPD1164	Approved
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.703	Intermediate Similarity	NPD3887	Approved
0.703	Intermediate Similarity	NPD2354	Approved
0.7024	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5691	Approved
0.7018	Intermediate Similarity	NPD6280	Approved
0.7018	Intermediate Similarity	NPD6279	Approved
0.7017	Intermediate Similarity	NPD4419	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