NPASS Compound

Structure

NPC234564 OpenBabel07101718192D 36 40 0 0 1 0 0 0 0 0999 V2000 -6.9047 3.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6176 1.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5665 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 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 1.7321 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 -0.0000 1.0000 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 -2.6831 -0.3090 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 -5.9266 2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 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 -3.2709 0.5000 0.0000 C 0 0 1 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 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 1 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 2.2321 -2.8660 0.0000 C 0 0 0 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 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 0.0000 -0.0000 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 -4.2709 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 2 0 0 0 0 5 27 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 30 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 19 4 1 1 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 20 32 1 6 0 0 0 21 24 1 0 0 0 0 21 33 1 6 0 0 0 22 29 1 6 0 0 0 22 30 1 0 0 0 0 23 29 1 6 0 0 0 23 34 1 0 0 0 0 24 27 1 6 0 0 0 25 28 1 1 0 0 0 25 31 1 0 0 0 0 26 29 1 0 0 0 0 26 35 2 0 0 0 0 26 36 1 0 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 7 1 6 0 0 0 30 31 1 1 0 0 0 31 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.37
Volume:	540.628
LogP:	4.417
LogD:	4.2
LogS:	-3.706
# Rotatable Bonds:	6
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	6.044
Fsp3:	0.903
Lipinski Rule-of-5:	Accepted
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:	-5.561
MDCK Permeability:	8.649969458929263e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.32
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.674
30% Bioavailability (F30%):	0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.586
Plasma Protein Binding (PPB):	91.77027893066406%
Volume Distribution (VD):	0.478
Pgp-substrate:	7.91701078414917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.459
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.189
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	3.759
Half-life (T1/2):	0.394

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.568
Maximum Recommended Daily Dose:	0.512
Skin Sensitization:	0.309
Carcinogencity:	0.543
Eye Corrosion:	0.018
Eye Irritation:	0.02
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC234564

Natural Product ID:	NPC234564
*Common Name:**	NMGCAUZQKXGUAO-ITRBRHPWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NMGCAUZQKXGUAO-ITRBRHPWSA-N
Standard InCHI:	InChI=1S/C31H50O5/c1-17(2)18(3)8-9-19(4)24-21(33)15-28(6)25-20(32)14-22-29(7,26(35)36)23(34)10-11-30(22)16-31(25,30)13-12-27(24,28)5/h17,19-25,32-34H,3,8-16H2,1-2,4-7H3,(H,35,36)/t19-,20+,21+,22+,23+,24+,25+,27-,28+,29+,30-,31+/m1/s1
SMILES:	C=C(C(C)C)CC[C@H]([C@H]1[C@@H](O)C[C@@]2([C@]1(C)CC[C@@]13[C@H]2[C@@H](O)C[C@@H]2[C@]3(C1)CC[C@@H]([C@@]2(C)C(=O)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468879
PubChem CID:	10918144
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO19294	Acalypha communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088430]
NPO19294	Acalypha communis	Species	Euphorbiaceae	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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[507794]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[507794]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	8.0	ug.mL-1	PMID[507794]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[507794]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16.0	ug.mL-1	PMID[507794]

☑ 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 NPC234564 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	223
0.1-0.2	1842
0.2-0.3	6553
0.3-0.4	14706
0.4-0.5	6666
0.5-0.6	5345
0.6-0.7	5188
0.7-0.8	1864
0.8-0.85	233
0.85-0.9	61
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC288906
0.9667	High Similarity	NPC263135
0.9468	High Similarity	NPC193934
0.9468	High Similarity	NPC271980
0.9255	High Similarity	NPC37047
0.9255	High Similarity	NPC41971
0.9255	High Similarity	NPC94906
0.9255	High Similarity	NPC180733
0.9239	High Similarity	NPC266431
0.9213	High Similarity	NPC146937
0.9158	High Similarity	NPC71706
0.9158	High Similarity	NPC75941
0.9149	High Similarity	NPC472028
0.9062	High Similarity	NPC124544
0.8969	High Similarity	NPC312900
0.8969	High Similarity	NPC470310
0.8913	High Similarity	NPC198242
0.8913	High Similarity	NPC211403
0.8901	High Similarity	NPC213832
0.8901	High Similarity	NPC57954
0.8889	High Similarity	NPC134197
0.8854	High Similarity	NPC108371
0.883	High Similarity	NPC205173
0.8817	High Similarity	NPC244356
0.8817	High Similarity	NPC224060
0.88	High Similarity	NPC211224
0.8791	High Similarity	NPC471900
0.8791	High Similarity	NPC183374
0.8791	High Similarity	NPC211162
0.8788	High Similarity	NPC265127
0.8778	High Similarity	NPC302111
0.8763	High Similarity	NPC289148
0.8763	High Similarity	NPC52899
0.8763	High Similarity	NPC163963
0.8737	High Similarity	NPC329910
0.8723	High Similarity	NPC470385
0.8723	High Similarity	NPC470386
0.8687	High Similarity	NPC201763
0.8681	High Similarity	NPC264005
0.8681	High Similarity	NPC269360
0.8673	High Similarity	NPC148628
0.8673	High Similarity	NPC88203
0.8673	High Similarity	NPC304832
0.8673	High Similarity	NPC76866
0.8673	High Similarity	NPC246736
0.8673	High Similarity	NPC214946
0.8673	High Similarity	NPC286519
0.866	High Similarity	NPC287676
0.8646	High Similarity	NPC469810
0.8646	High Similarity	NPC253586
0.8632	High Similarity	NPC470232
0.8632	High Similarity	NPC470229
0.8632	High Similarity	NPC48330
0.8617	High Similarity	NPC144739
0.8617	High Similarity	NPC181594
0.8617	High Similarity	NPC473690
0.8617	High Similarity	NPC477855
0.8617	High Similarity	NPC471902
0.8617	High Similarity	NPC287118
0.8602	High Similarity	NPC169933
0.86	High Similarity	NPC295366
0.86	High Similarity	NPC37600
0.8586	High Similarity	NPC469985
0.8586	High Similarity	NPC87927
0.8571	High Similarity	NPC80590
0.8571	High Similarity	NPC253886
0.8571	High Similarity	NPC2783
0.8571	High Similarity	NPC46848
0.8571	High Similarity	NPC121218
0.8557	High Similarity	NPC474793
0.8557	High Similarity	NPC16911
0.8557	High Similarity	NPC471038
0.8557	High Similarity	NPC78427
0.8544	High Similarity	NPC470281
0.8542	High Similarity	NPC13949
0.8542	High Similarity	NPC173272
0.8542	High Similarity	NPC470387
0.8542	High Similarity	NPC327788
0.8526	High Similarity	NPC475118
0.8526	High Similarity	NPC47853
0.8526	High Similarity	NPC292374
0.8526	High Similarity	NPC129004
0.8526	High Similarity	NPC91772
0.8526	High Similarity	NPC261333
0.8526	High Similarity	NPC289539
0.8526	High Similarity	NPC111524
0.8526	High Similarity	NPC153775
0.8526	High Similarity	NPC104371
0.8526	High Similarity	NPC277399
0.8526	High Similarity	NPC101233
0.8526	High Similarity	NPC29247
0.8526	High Similarity	NPC215271
0.8515	High Similarity	NPC263729
0.8511	High Similarity	NPC471901
0.8511	High Similarity	NPC299185
0.8511	High Similarity	NPC475416
0.8511	High Similarity	NPC476168
0.85	High Similarity	NPC98603
0.8495	Intermediate Similarity	NPC56962
0.8495	Intermediate Similarity	NPC24772
0.8495	Intermediate Similarity	NPC24705
0.8495	Intermediate Similarity	NPC116146
0.8485	Intermediate Similarity	NPC170615
0.8485	Intermediate Similarity	NPC275990
0.8478	Intermediate Similarity	NPC259009
0.8478	Intermediate Similarity	NPC57469
0.8478	Intermediate Similarity	NPC33768
0.8462	Intermediate Similarity	NPC264317
0.8462	Intermediate Similarity	NPC294438
0.8454	Intermediate Similarity	NPC170978
0.8444	Intermediate Similarity	NPC245866
0.8438	Intermediate Similarity	NPC231060
0.8438	Intermediate Similarity	NPC98639
0.8438	Intermediate Similarity	NPC210214
0.8438	Intermediate Similarity	NPC138245
0.8438	Intermediate Similarity	NPC84018
0.8431	Intermediate Similarity	NPC163216
0.8421	Intermediate Similarity	NPC291373
0.8421	Intermediate Similarity	NPC294263
0.8404	Intermediate Similarity	NPC261994
0.8404	Intermediate Similarity	NPC100313
0.8404	Intermediate Similarity	NPC80401
0.8404	Intermediate Similarity	NPC470378
0.8404	Intermediate Similarity	NPC180849
0.8404	Intermediate Similarity	NPC149761
0.84	Intermediate Similarity	NPC216114
0.8387	Intermediate Similarity	NPC474719
0.8387	Intermediate Similarity	NPC16377
0.8384	Intermediate Similarity	NPC39683
0.8384	Intermediate Similarity	NPC471790
0.8384	Intermediate Similarity	NPC295276
0.8384	Intermediate Similarity	NPC236585
0.837	Intermediate Similarity	NPC70661
0.837	Intermediate Similarity	NPC12774
0.8367	Intermediate Similarity	NPC98837
0.8367	Intermediate Similarity	NPC38296
0.8367	Intermediate Similarity	NPC477854
0.8367	Intermediate Similarity	NPC28864
0.8367	Intermediate Similarity	NPC20479
0.8367	Intermediate Similarity	NPC162459
0.8367	Intermediate Similarity	NPC38471
0.8365	Intermediate Similarity	NPC470311
0.8365	Intermediate Similarity	NPC270586
0.8351	Intermediate Similarity	NPC200054
0.8351	Intermediate Similarity	NPC135548
0.8351	Intermediate Similarity	NPC140242
0.8351	Intermediate Similarity	NPC29410
0.8351	Intermediate Similarity	NPC264979
0.8351	Intermediate Similarity	NPC477853
0.835	Intermediate Similarity	NPC257082
0.835	Intermediate Similarity	NPC285298
0.8333	Intermediate Similarity	NPC280804
0.8333	Intermediate Similarity	NPC302008
0.8333	Intermediate Similarity	NPC191094
0.8317	Intermediate Similarity	NPC84928
0.8317	Intermediate Similarity	NPC47281
0.8316	Intermediate Similarity	NPC250753
0.8316	Intermediate Similarity	NPC470230
0.8315	Intermediate Similarity	NPC477851
0.83	Intermediate Similarity	NPC15396
0.8298	Intermediate Similarity	NPC475921
0.8298	Intermediate Similarity	NPC474704
0.8298	Intermediate Similarity	NPC220498
0.8283	Intermediate Similarity	NPC470388
0.8283	Intermediate Similarity	NPC293866
0.828	Intermediate Similarity	NPC153604
0.828	Intermediate Similarity	NPC472497
0.8265	Intermediate Similarity	NPC10864
0.8265	Intermediate Similarity	NPC111187
0.8265	Intermediate Similarity	NPC190554
0.8265	Intermediate Similarity	NPC190080
0.8261	Intermediate Similarity	NPC201655
0.8261	Intermediate Similarity	NPC76518
0.8261	Intermediate Similarity	NPC190704
0.8261	Intermediate Similarity	NPC471034
0.8252	Intermediate Similarity	NPC231278
0.8252	Intermediate Similarity	NPC218123
0.8252	Intermediate Similarity	NPC112895
0.8247	Intermediate Similarity	NPC279974
0.8242	Intermediate Similarity	NPC471037
0.8235	Intermediate Similarity	NPC138908
0.8235	Intermediate Similarity	NPC278628
0.8235	Intermediate Similarity	NPC28791
0.8235	Intermediate Similarity	NPC231530
0.8235	Intermediate Similarity	NPC50535
0.8235	Intermediate Similarity	NPC285927
0.8235	Intermediate Similarity	NPC200957
0.8229	Intermediate Similarity	NPC59350
0.8229	Intermediate Similarity	NPC470375
0.8229	Intermediate Similarity	NPC59170
0.8229	Intermediate Similarity	NPC206810
0.8229	Intermediate Similarity	NPC476189
0.8229	Intermediate Similarity	NPC470376
0.8218	Intermediate Similarity	NPC122811
0.8218	Intermediate Similarity	NPC139347
0.8218	Intermediate Similarity	NPC209298
0.8218	Intermediate Similarity	NPC277074
0.8211	Intermediate Similarity	NPC77756
0.8211	Intermediate Similarity	NPC46758
0.8191	Intermediate Similarity	NPC160304

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 NPC234564 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	2286
0.2-0.3	4081
0.3-0.4	1729
0.4-0.5	392
0.5-0.6	189
0.6-0.7	166
0.7-0.8	96
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD6697	Approved
0.809	Intermediate Similarity	NPD6114	Approved
0.809	Intermediate Similarity	NPD6118	Approved
0.809	Intermediate Similarity	NPD6115	Approved
0.7938	Intermediate Similarity	NPD8035	Phase 2
0.7938	Intermediate Similarity	NPD8034	Phase 2
0.7885	Intermediate Similarity	NPD6402	Approved
0.7885	Intermediate Similarity	NPD5739	Approved
0.7885	Intermediate Similarity	NPD7128	Approved
0.7885	Intermediate Similarity	NPD6675	Approved
0.7865	Intermediate Similarity	NPD6117	Approved
0.7778	Intermediate Similarity	NPD6116	Phase 1
0.7736	Intermediate Similarity	NPD6899	Approved
0.7736	Intermediate Similarity	NPD7320	Approved
0.7736	Intermediate Similarity	NPD6881	Approved
0.7732	Intermediate Similarity	NPD5328	Approved
0.7723	Intermediate Similarity	NPD4755	Approved
0.7664	Intermediate Similarity	NPD6372	Approved
0.7664	Intermediate Similarity	NPD6373	Approved
0.766	Intermediate Similarity	NPD4788	Approved
0.7647	Intermediate Similarity	NPD7638	Approved
0.7642	Intermediate Similarity	NPD5697	Approved
0.7642	Intermediate Similarity	NPD5701	Approved
0.764	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7290	Approved
0.7593	Intermediate Similarity	NPD4634	Approved
0.7593	Intermediate Similarity	NPD7102	Approved
0.7593	Intermediate Similarity	NPD6883	Approved
0.7576	Intermediate Similarity	NPD6079	Approved
0.7573	Intermediate Similarity	NPD7640	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.7573	Intermediate Similarity	NPD5285	Approved
0.7573	Intermediate Similarity	NPD5286	Approved
0.7573	Intermediate Similarity	NPD4700	Approved
0.7573	Intermediate Similarity	NPD4696	Approved
0.7556	Intermediate Similarity	NPD3703	Phase 2
0.7523	Intermediate Similarity	NPD8130	Phase 1
0.7523	Intermediate Similarity	NPD6617	Approved
0.7523	Intermediate Similarity	NPD6650	Approved
0.7523	Intermediate Similarity	NPD6869	Approved
0.7523	Intermediate Similarity	NPD6649	Approved
0.7523	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.7456	Intermediate Similarity	NPD6319	Approved
0.7455	Intermediate Similarity	NPD8297	Approved
0.7455	Intermediate Similarity	NPD6882	Approved
0.7429	Intermediate Similarity	NPD4633	Approved
0.7429	Intermediate Similarity	NPD5225	Approved
0.7429	Intermediate Similarity	NPD5224	Approved
0.7429	Intermediate Similarity	NPD5226	Approved
0.7429	Intermediate Similarity	NPD5211	Phase 2
0.7407	Intermediate Similarity	NPD6011	Approved
0.74	Intermediate Similarity	NPD7515	Phase 2
0.7396	Intermediate Similarity	NPD4786	Approved
0.7387	Intermediate Similarity	NPD4632	Approved
0.7383	Intermediate Similarity	NPD6008	Approved
0.7379	Intermediate Similarity	NPD6084	Phase 2
0.7379	Intermediate Similarity	NPD6083	Phase 2
0.7364	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5175	Approved
0.7358	Intermediate Similarity	NPD5174	Approved
0.735	Intermediate Similarity	NPD7492	Approved
0.7333	Intermediate Similarity	NPD5223	Approved
0.7327	Intermediate Similarity	NPD4202	Approved
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.7311	Intermediate Similarity	NPD7736	Approved
0.7304	Intermediate Similarity	NPD6054	Approved
0.7304	Intermediate Similarity	NPD6059	Approved
0.729	Intermediate Similarity	NPD5141	Approved
0.7288	Intermediate Similarity	NPD6616	Approved
0.7282	Intermediate Similarity	NPD4697	Phase 3
0.7282	Intermediate Similarity	NPD5222	Approved
0.7282	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5221	Approved
0.7265	Intermediate Similarity	NPD7604	Phase 2
0.725	Intermediate Similarity	NPD7319	Approved
0.7245	Intermediate Similarity	NPD3618	Phase 1
0.7227	Intermediate Similarity	NPD7078	Approved
0.7227	Intermediate Similarity	NPD8293	Discontinued
0.7222	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4768	Approved
0.7222	Intermediate Similarity	NPD4767	Approved
0.7216	Intermediate Similarity	NPD3665	Phase 1
0.7216	Intermediate Similarity	NPD3666	Approved
0.7216	Intermediate Similarity	NPD3133	Approved
0.7212	Intermediate Similarity	NPD5173	Approved
0.72	Intermediate Similarity	NPD4753	Phase 2
0.7196	Intermediate Similarity	NPD4754	Approved
0.7193	Intermediate Similarity	NPD6009	Approved
0.7188	Intermediate Similarity	NPD3667	Approved
0.7184	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6370	Approved
0.7158	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD7507	Approved
0.7111	Intermediate Similarity	NPD4245	Approved
0.7111	Intermediate Similarity	NPD4244	Approved
0.7105	Intermediate Similarity	NPD6274	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.71	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6016	Approved
0.7094	Intermediate Similarity	NPD6015	Approved
0.7091	Intermediate Similarity	NPD4729	Approved
0.7091	Intermediate Similarity	NPD5128	Approved
0.7091	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4730	Approved
0.7087	Intermediate Similarity	NPD7748	Approved
0.708	Intermediate Similarity	NPD8133	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7069	Intermediate Similarity	NPD7100	Approved
0.7069	Intermediate Similarity	NPD7101	Approved
0.7059	Intermediate Similarity	NPD6411	Approved
0.7043	Intermediate Similarity	NPD7115	Discovery
0.7034	Intermediate Similarity	NPD5988	Approved
0.7019	Intermediate Similarity	NPD5695	Phase 3
0.7	Intermediate Similarity	NPD3698	Phase 2
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3702	Approved
0.6983	Remote Similarity	NPD6335	Approved
0.6981	Remote Similarity	NPD5696	Approved
0.6964	Remote Similarity	NPD5247	Approved
0.6964	Remote Similarity	NPD5248	Approved
0.6964	Remote Similarity	NPD5250	Approved
0.6964	Remote Similarity	NPD5249	Phase 3
0.6964	Remote Similarity	NPD5251	Approved
0.6949	Remote Similarity	NPD6908	Approved
0.6949	Remote Similarity	NPD6909	Approved
0.6949	Remote Similarity	NPD5983	Phase 2
0.6931	Remote Similarity	NPD6903	Approved
0.6903	Remote Similarity	NPD5217	Approved
0.6903	Remote Similarity	NPD5216	Approved
0.6903	Remote Similarity	NPD5215	Approved
0.69	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6317	Approved
0.6893	Remote Similarity	NPD7637	Suspended
0.6887	Remote Similarity	NPD7902	Approved
0.6863	Remote Similarity	NPD6101	Approved
0.6863	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6336	Discontinued
0.6857	Remote Similarity	NPD5210	Approved
0.6857	Remote Similarity	NPD4629	Approved
0.6848	Remote Similarity	NPD6081	Approved
0.6848	Remote Similarity	NPD5777	Approved
0.6847	Remote Similarity	NPD6412	Phase 2
0.6838	Remote Similarity	NPD6313	Approved
0.6838	Remote Similarity	NPD6314	Approved
0.6837	Remote Similarity	NPD4221	Approved
0.6837	Remote Similarity	NPD4223	Phase 3
0.6827	Remote Similarity	NPD5779	Approved
0.6827	Remote Similarity	NPD5778	Approved
0.6814	Remote Similarity	NPD5135	Approved
0.6814	Remote Similarity	NPD5169	Approved
0.6814	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6868	Approved
0.6804	Remote Similarity	NPD5368	Approved
0.68	Remote Similarity	NPD5329	Approved
0.6765	Remote Similarity	NPD6672	Approved
0.6765	Remote Similarity	NPD5737	Approved
0.6762	Remote Similarity	NPD6001	Approved
0.6754	Remote Similarity	NPD5127	Approved
0.6752	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6033	Approved
0.6739	Remote Similarity	NPD4789	Approved
0.6737	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6098	Approved
0.6731	Remote Similarity	NPD5281	Approved
0.6731	Remote Similarity	NPD5284	Approved
0.6703	Remote Similarity	NPD5360	Phase 3
0.6703	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3668	Phase 3
0.67	Remote Similarity	NPD4197	Approved
0.6699	Remote Similarity	NPD6673	Approved
0.6699	Remote Similarity	NPD6080	Approved
0.6699	Remote Similarity	NPD6904	Approved
0.6697	Remote Similarity	NPD1700	Approved
0.6696	Remote Similarity	NPD6053	Discontinued
0.6694	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4224	Phase 2
0.6637	Remote Similarity	NPD5168	Approved
0.6632	Remote Similarity	NPD7339	Approved
0.6632	Remote Similarity	NPD6942	Approved
0.663	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8418	Phase 2
0.6604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7900	Approved
0.6581	Remote Similarity	NPD5167	Approved
0.6579	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5786	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