NPASS Compound

Structure

NPC204644 OpenBabel07101719252D 40 43 0 0 1 0 0 0 0 0999 V2000 -0.0000 -0.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -0.0000 -1.0000 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 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 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 -3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 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 0.0000 2.0000 0.0000 C 0 0 1 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 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 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 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 O 0 0 0 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 0.0000 3.0000 0.0000 O 0 0 0 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 11 1 0 0 0 0 5 16 2 0 0 0 0 6 9 1 0 0 0 0 6 17 2 0 0 0 0 7 10 2 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 31 1 0 0 0 0 16 24 1 0 0 0 0 18 32 1 0 0 0 0 19 15 1 6 0 0 0 19 28 1 0 0 0 0 20 14 1 1 0 0 0 20 25 1 0 0 0 0 20 38 1 0 0 0 0 21 30 1 6 0 0 0 21 33 1 0 0 0 0 22 30 1 6 0 0 0 22 39 1 0 0 0 0 23 34 2 0 0 0 0 23 39 1 0 0 0 0 24 28 1 0 0 0 0 24 30 1 6 0 0 0 25 26 1 0 0 0 0 25 35 1 6 0 0 0 26 27 1 0 0 0 0 26 36 1 1 0 0 0 27 29 1 0 0 0 0 27 37 1 6 0 0 0 28 40 1 6 0 0 0 29 38 1 0 0 0 0 29 40 1 1 0 0 0 30 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.28
Volume:	565.294
LogP:	3.09
LogD:	2.437
LogS:	-3.501
# Rotatable Bonds:	8
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	4.998
Fsp3:	0.633
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.994
MDCK Permeability:	5.1987448387080804e-05
Pgp-inhibitor:	0.057
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.882
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	94.8222427368164%
Volume Distribution (VD):	0.571
Pgp-substrate:	5.714666843414307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.172
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	5.103
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.546
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.567
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.645
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC204644

Natural Product ID:	NPC204644
*Common Name:**	9Beta-O-(E-P-Hydroxycinnamoyl)-1Beta,6Beta-Dihydroxy-Trans-Eudesm-3-En-6-O-Beta-D-Glucopyranoside
IUPAC Name:	[(1S,3S,4R,4aS,8R,8aR)-8-hydroxy-5,8a-dimethyl-3-propan-2-yl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,4a,7,8-hexahydro-1H-naphthalen-1-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	FYIRTYWAWSCPCM-RQDXIEOQSA-N
Standard InCHI:	InChI=1S/C30H42O10/c1-15(2)19-13-22(39-23(34)12-8-17-6-9-18(32)10-7-17)30(4)21(33)11-5-16(3)24(30)28(19)40-29-27(37)26(36)25(35)20(14-31)38-29/h5-10,12,15,19-22,24-29,31-33,35-37H,11,13-14H2,1-4H3/b12-8+/t19-,20+,21+,22-,24+,25+,26-,27+,28+,29-,30+/m0/s1
SMILES:	CC(C)[C@@H]1C[C@@H]([C@@]2(C)[C@@H](CC=C(C)[C@@H]2[C@@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)OC(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011643
PubChem CID:	57333878
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO23708	Aster koraiensis	Species	Asteraceae	Eukaryota	aerial parts	Euidang-myun, Gongju city, Chungchengnam-do, Republic of Korea	2007-Aug	PMID[22264115]
NPO23708	Aster koraiensis	Species	Asteraceae	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
IC50	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	>	50000.0	nM	PMID[479575]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	30000.0	nM	PMID[479575]

☑ 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 NPC204644 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	312
0.1-0.2	1278
0.2-0.3	2628
0.3-0.4	5199
0.4-0.5	8942
0.5-0.6	10052
0.6-0.7	10862
0.7-0.8	3130
0.8-0.85	245
0.85-0.9	44
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9362	High Similarity	NPC320734
0.9028	High Similarity	NPC470330
0.8912	High Similarity	NPC77310
0.8905	High Similarity	NPC235294
0.8905	High Similarity	NPC46137
0.8819	High Similarity	NPC96447
0.8768	High Similarity	NPC225384
0.8768	High Similarity	NPC138777
0.8768	High Similarity	NPC246869
0.875	High Similarity	NPC288416
0.8732	High Similarity	NPC197316
0.8732	High Similarity	NPC64141
0.8732	High Similarity	NPC472350
0.8732	High Similarity	NPC476383
0.8732	High Similarity	NPC68092
0.8732	High Similarity	NPC89105
0.8732	High Similarity	NPC81515
0.8716	High Similarity	NPC116292
0.8716	High Similarity	NPC87630
0.8716	High Similarity	NPC179128
0.8716	High Similarity	NPC267469
0.8693	High Similarity	NPC269668
0.8676	High Similarity	NPC471157
0.8671	High Similarity	NPC470617
0.8671	High Similarity	NPC470616
0.8667	High Similarity	NPC474532
0.8662	High Similarity	NPC260425
0.8652	High Similarity	NPC263829
0.8633	High Similarity	NPC478255
0.8613	High Similarity	NPC106677
0.8611	High Similarity	NPC47471
0.8611	High Similarity	NPC476377
0.8611	High Similarity	NPC476385
0.8611	High Similarity	NPC134405
0.8603	High Similarity	NPC126991
0.8603	High Similarity	NPC83218
0.8601	High Similarity	NPC205195
0.8601	High Similarity	NPC116742
0.8601	High Similarity	NPC139243
0.8592	High Similarity	NPC154485
0.8592	High Similarity	NPC471872
0.8591	High Similarity	NPC162569
0.8591	High Similarity	NPC35160
0.8582	High Similarity	NPC34293
0.8582	High Similarity	NPC886
0.8582	High Similarity	NPC287597
0.8552	High Similarity	NPC265648
0.8552	High Similarity	NPC222433
0.8551	High Similarity	NPC225307
0.8543	High Similarity	NPC471874
0.8542	High Similarity	NPC475530
0.8542	High Similarity	NPC473799
0.8542	High Similarity	NPC164743
0.854	High Similarity	NPC252114
0.8535	High Similarity	NPC469459
0.8535	High Similarity	NPC469458
0.8535	High Similarity	NPC88176
0.8535	High Similarity	NPC149002
0.8535	High Similarity	NPC469396
0.8531	High Similarity	NPC476376
0.8531	High Similarity	NPC78363
0.8519	High Similarity	NPC52097
0.8493	Intermediate Similarity	NPC298257
0.8493	Intermediate Similarity	NPC96795
0.8493	Intermediate Similarity	NPC476384
0.8493	Intermediate Similarity	NPC112
0.8493	Intermediate Similarity	NPC119537
0.8493	Intermediate Similarity	NPC247032
0.8493	Intermediate Similarity	NPC476380
0.8493	Intermediate Similarity	NPC175214
0.8493	Intermediate Similarity	NPC76406
0.8493	Intermediate Similarity	NPC476375
0.8493	Intermediate Similarity	NPC269141
0.8493	Intermediate Similarity	NPC264632
0.8493	Intermediate Similarity	NPC476381
0.8493	Intermediate Similarity	NPC476378
0.8493	Intermediate Similarity	NPC476397
0.8493	Intermediate Similarity	NPC205864
0.8478	Intermediate Similarity	NPC471882
0.8478	Intermediate Similarity	NPC45224
0.8478	Intermediate Similarity	NPC471881
0.8478	Intermediate Similarity	NPC156692
0.8478	Intermediate Similarity	NPC173150
0.8478	Intermediate Similarity	NPC230331
0.8478	Intermediate Similarity	NPC35288
0.8472	Intermediate Similarity	NPC321184
0.8472	Intermediate Similarity	NPC321638
0.8472	Intermediate Similarity	NPC328273
0.8472	Intermediate Similarity	NPC171134
0.8467	Intermediate Similarity	NPC12006
0.8456	Intermediate Similarity	NPC95990
0.8451	Intermediate Similarity	NPC169398
0.8446	Intermediate Similarity	NPC208293
0.8444	Intermediate Similarity	NPC11724
0.844	Intermediate Similarity	NPC473285
0.8435	Intermediate Similarity	NPC26045
0.8435	Intermediate Similarity	NPC296659
0.8435	Intermediate Similarity	NPC202391
0.8435	Intermediate Similarity	NPC300894
0.8435	Intermediate Similarity	NPC141455
0.8435	Intermediate Similarity	NPC296954
0.8435	Intermediate Similarity	NPC196063
0.8435	Intermediate Similarity	NPC251062
0.8435	Intermediate Similarity	NPC64195
0.8435	Intermediate Similarity	NPC184464
0.8421	Intermediate Similarity	NPC257847
0.8418	Intermediate Similarity	NPC469419
0.8414	Intermediate Similarity	NPC271494
0.8414	Intermediate Similarity	NPC473591
0.8414	Intermediate Similarity	NPC155192
0.8406	Intermediate Similarity	NPC61181
0.8403	Intermediate Similarity	NPC65262
0.8403	Intermediate Similarity	NPC469364
0.8403	Intermediate Similarity	NPC101686
0.8397	Intermediate Similarity	NPC117943
0.8397	Intermediate Similarity	NPC477627
0.8397	Intermediate Similarity	NPC293568
0.8394	Intermediate Similarity	NPC265413
0.8394	Intermediate Similarity	NPC10154
0.8392	Intermediate Similarity	NPC476870
0.8389	Intermediate Similarity	NPC97240
0.838	Intermediate Similarity	NPC28637
0.8378	Intermediate Similarity	NPC100998
0.8378	Intermediate Similarity	NPC34927
0.8378	Intermediate Similarity	NPC252292
0.8378	Intermediate Similarity	NPC34587
0.8378	Intermediate Similarity	NPC476382
0.837	Intermediate Similarity	NPC476872
0.8369	Intermediate Similarity	NPC254819
0.8367	Intermediate Similarity	NPC235557
0.8367	Intermediate Similarity	NPC105005
0.8365	Intermediate Similarity	NPC286809
0.8357	Intermediate Similarity	NPC477293
0.8357	Intermediate Similarity	NPC477294
0.8357	Intermediate Similarity	NPC86257
0.8357	Intermediate Similarity	NPC229784
0.8356	Intermediate Similarity	NPC27518
0.8356	Intermediate Similarity	NPC304110
0.8355	Intermediate Similarity	NPC478268
0.8345	Intermediate Similarity	NPC182249
0.8345	Intermediate Similarity	NPC103533
0.8333	Intermediate Similarity	NPC470733
0.8323	Intermediate Similarity	NPC135334
0.8323	Intermediate Similarity	NPC469777
0.8323	Intermediate Similarity	NPC469778
0.8323	Intermediate Similarity	NPC32723
0.8323	Intermediate Similarity	NPC469774
0.8323	Intermediate Similarity	NPC469773
0.8323	Intermediate Similarity	NPC469776
0.8323	Intermediate Similarity	NPC100925
0.8323	Intermediate Similarity	NPC477617
0.8323	Intermediate Similarity	NPC469775
0.8323	Intermediate Similarity	NPC148185
0.8323	Intermediate Similarity	NPC295941
0.8323	Intermediate Similarity	NPC469772
0.8322	Intermediate Similarity	NPC471883
0.8322	Intermediate Similarity	NPC229505
0.8321	Intermediate Similarity	NPC470815
0.8313	Intermediate Similarity	NPC471870
0.8311	Intermediate Similarity	NPC25491
0.8309	Intermediate Similarity	NPC469686
0.8299	Intermediate Similarity	NPC296643
0.8299	Intermediate Similarity	NPC140502
0.8299	Intermediate Similarity	NPC145319
0.8286	Intermediate Similarity	NPC232880
0.8282	Intermediate Similarity	NPC475613
0.8276	Intermediate Similarity	NPC22676
0.8276	Intermediate Similarity	NPC475482
0.8276	Intermediate Similarity	NPC216940
0.8276	Intermediate Similarity	NPC198621
0.8269	Intermediate Similarity	NPC478269
0.8267	Intermediate Similarity	NPC232992
0.8255	Intermediate Similarity	NPC286245
0.8255	Intermediate Similarity	NPC138915
0.8255	Intermediate Similarity	NPC272619
0.8252	Intermediate Similarity	NPC254398
0.8243	Intermediate Similarity	NPC186296
0.8243	Intermediate Similarity	NPC40305
0.8239	Intermediate Similarity	NPC473047
0.8239	Intermediate Similarity	NPC219677
0.8239	Intermediate Similarity	NPC265600
0.8235	Intermediate Similarity	NPC469704
0.8235	Intermediate Similarity	NPC201402
0.8235	Intermediate Similarity	NPC469703
0.8235	Intermediate Similarity	NPC160854
0.8231	Intermediate Similarity	NPC7518
0.8231	Intermediate Similarity	NPC159387
0.8231	Intermediate Similarity	NPC475513
0.8231	Intermediate Similarity	NPC137501
0.8231	Intermediate Similarity	NPC473755
0.8231	Intermediate Similarity	NPC154262
0.8227	Intermediate Similarity	NPC253595
0.8219	Intermediate Similarity	NPC475757
0.8219	Intermediate Similarity	NPC49597
0.8219	Intermediate Similarity	NPC474640
0.8214	Intermediate Similarity	NPC476873
0.821	Intermediate Similarity	NPC13989
0.8207	Intermediate Similarity	NPC166180
0.8207	Intermediate Similarity	NPC471345
0.8207	Intermediate Similarity	NPC249817

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 NPC204644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	781
0.2-0.3	1570
0.3-0.4	2803
0.4-0.5	2061
0.5-0.6	1215
0.6-0.7	425
0.7-0.8	39
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8732	High Similarity	NPD7266	Discontinued
0.7815	Intermediate Similarity	NPD8166	Discontinued
0.7697	Intermediate Similarity	NPD7228	Approved
0.7692	Intermediate Similarity	NPD1653	Approved
0.7632	Intermediate Similarity	NPD6674	Discontinued
0.7562	Intermediate Similarity	NPD8455	Phase 2
0.7544	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7469	Intermediate Similarity	NPD4967	Phase 2
0.7469	Intermediate Similarity	NPD4965	Approved
0.7469	Intermediate Similarity	NPD4966	Approved
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7466	Intermediate Similarity	NPD5736	Approved
0.7448	Intermediate Similarity	NPD3094	Phase 2
0.744	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7458	Discontinued
0.7419	Intermediate Similarity	NPD6190	Approved
0.7417	Intermediate Similarity	NPD7097	Phase 1
0.7394	Intermediate Similarity	NPD8127	Discontinued
0.7394	Intermediate Similarity	NPD5126	Approved
0.7394	Intermediate Similarity	NPD5125	Phase 3
0.7355	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4060	Phase 1
0.731	Intermediate Similarity	NPD7240	Approved
0.731	Intermediate Similarity	NPD7685	Pre-registration
0.731	Intermediate Similarity	NPD6559	Discontinued
0.7303	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1091	Approved
0.7292	Intermediate Similarity	NPD3092	Approved
0.7273	Intermediate Similarity	NPD5763	Approved
0.7273	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD6663	Approved
0.7235	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4140	Approved
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8150	Discontinued
0.72	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7074	Phase 3
0.7176	Intermediate Similarity	NPD7799	Discontinued
0.7171	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD8651	Approved
0.7135	Intermediate Similarity	NPD5844	Phase 1
0.7135	Intermediate Similarity	NPD7054	Approved
0.7133	Intermediate Similarity	NPD3091	Approved
0.7125	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2861	Phase 2
0.7108	Intermediate Similarity	NPD7075	Discontinued
0.7102	Intermediate Similarity	NPD8434	Phase 2
0.7093	Intermediate Similarity	NPD7472	Approved
0.7086	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4908	Phase 1
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5735	Approved
0.7048	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7157	Approved
0.7034	Intermediate Similarity	NPD4626	Approved
0.7027	Intermediate Similarity	NPD7435	Discontinued
0.702	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7095	Approved
0.702	Intermediate Similarity	NPD3027	Phase 3
0.7019	Intermediate Similarity	NPD6273	Approved
0.7011	Intermediate Similarity	NPD7251	Discontinued
0.7	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3620	Phase 2
0.6993	Remote Similarity	NPD1613	Approved
0.6993	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8319	Approved
0.6989	Remote Similarity	NPD8320	Phase 1
0.6982	Remote Similarity	NPD7199	Phase 2
0.6977	Remote Similarity	NPD3818	Discontinued
0.6974	Remote Similarity	NPD3764	Approved
0.6971	Remote Similarity	NPD7808	Phase 3
0.6966	Remote Similarity	NPD5691	Approved
0.6966	Remote Similarity	NPD7503	Approved
0.6962	Remote Similarity	NPD1652	Phase 2
0.6961	Remote Similarity	NPD6534	Approved
0.6961	Remote Similarity	NPD6535	Approved
0.6957	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6797	Phase 2
0.6951	Remote Similarity	NPD7028	Phase 2
0.6948	Remote Similarity	NPD6355	Discontinued
0.694	Remote Similarity	NPD7699	Phase 2
0.694	Remote Similarity	NPD7700	Phase 2
0.6937	Remote Similarity	NPD7236	Approved
0.6937	Remote Similarity	NPD5058	Phase 3
0.6928	Remote Similarity	NPD7819	Suspended
0.6928	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4198	Discontinued
0.6918	Remote Similarity	NPD7003	Approved
0.6918	Remote Similarity	NPD2932	Approved
0.6918	Remote Similarity	NPD3095	Discontinued
0.6918	Remote Similarity	NPD3750	Approved
0.6914	Remote Similarity	NPD8368	Discontinued
0.6902	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7741	Discontinued
0.689	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6823	Phase 2
0.6879	Remote Similarity	NPD3751	Discontinued
0.6879	Remote Similarity	NPD2935	Discontinued
0.6875	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3496	Discontinued
0.6865	Remote Similarity	NPD6782	Approved
0.6865	Remote Similarity	NPD6780	Approved
0.6865	Remote Similarity	NPD6778	Approved
0.6865	Remote Similarity	NPD6781	Approved
0.6865	Remote Similarity	NPD6779	Approved
0.6865	Remote Similarity	NPD6776	Approved
0.6865	Remote Similarity	NPD6777	Approved
0.6853	Remote Similarity	NPD2629	Approved
0.6845	Remote Similarity	NPD7680	Approved
0.6829	Remote Similarity	NPD7239	Suspended
0.6824	Remote Similarity	NPD3705	Approved
0.6824	Remote Similarity	NPD1610	Phase 2
0.6821	Remote Similarity	NPD7473	Discontinued
0.6818	Remote Similarity	NPD6233	Phase 2
0.6815	Remote Similarity	NPD4108	Discontinued
0.6813	Remote Similarity	NPD6213	Phase 3
0.6813	Remote Similarity	NPD6212	Phase 3
0.6813	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7874	Approved
0.6806	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3019	Approved
0.6802	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8407	Phase 2
0.6795	Remote Similarity	NPD6653	Approved
0.6786	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5402	Approved
0.6781	Remote Similarity	NPD9545	Approved
0.6772	Remote Similarity	NPD6100	Approved
0.6772	Remote Similarity	NPD5408	Approved
0.6772	Remote Similarity	NPD2438	Suspended
0.6772	Remote Similarity	NPD5406	Approved
0.6772	Remote Similarity	NPD5404	Approved
0.6772	Remote Similarity	NPD6099	Approved
0.6772	Remote Similarity	NPD5405	Approved
0.6771	Remote Similarity	NPD7783	Phase 2
0.6771	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6801	Discontinued
0.6761	Remote Similarity	NPD969	Suspended
0.6755	Remote Similarity	NPD7697	Approved
0.6755	Remote Similarity	NPD7698	Approved
0.6755	Remote Similarity	NPD7696	Phase 3
0.6754	Remote Similarity	NPD8151	Discontinued
0.6753	Remote Similarity	NPD6798	Discontinued
0.6752	Remote Similarity	NPD4538	Approved
0.6752	Remote Similarity	NPD4536	Approved
0.6752	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6599	Discontinued
0.6746	Remote Similarity	NPD7768	Phase 2
0.6744	Remote Similarity	NPD6232	Discontinued
0.674	Remote Similarity	NPD8361	Approved
0.674	Remote Similarity	NPD8360	Approved
0.6738	Remote Similarity	NPD3021	Approved
0.6738	Remote Similarity	NPD3022	Approved
0.6735	Remote Similarity	NPD1357	Approved
0.6733	Remote Similarity	NPD5327	Phase 3
0.6733	Remote Similarity	NPD4749	Approved
0.6732	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4340	Discontinued
0.6731	Remote Similarity	NPD230	Phase 1
0.673	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7871	Phase 2
0.672	Remote Similarity	NPD7870	Phase 2
0.6714	Remote Similarity	NPD1358	Approved
0.6713	Remote Similarity	NPD7635	Approved
0.6713	Remote Similarity	NPD7843	Approved
0.6711	Remote Similarity	NPD422	Phase 1
0.6708	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4110	Phase 3
0.6707	Remote Similarity	NPD7411	Suspended
0.6702	Remote Similarity	NPD7701	Phase 2
0.6691	Remote Similarity	NPD3020	Approved
0.6689	Remote Similarity	NPD6696	Suspended
0.6688	Remote Similarity	NPD4625	Phase 3
0.6687	Remote Similarity	NPD2424	Discontinued
0.6684	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6980	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