NPASS Compound

Structure

NPC470388 OpenBabel07101718192D 27 30 0 0 1 0 0 0 0 0999 V2000 3.5072 1.2414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1526 -1.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3342 -2.8325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0299 1.5847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5323 1.0643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6074 -1.0893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9381 0.9324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5561 0.9324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7471 1.5202 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6289 0.3507 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2363 -0.7387 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2471 -0.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1527 -1.9441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 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 1.2471 -0.0187 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1055 0.5316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0948 -1.2516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8349 -0.8277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6032 1.3692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6656 -2.8025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -1.9591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 5 1 1 0 0 0 12 17 1 0 0 0 0 12 22 1 6 0 0 0 13 20 1 6 0 0 0 13 21 1 0 0 0 0 14 19 1 6 0 0 0 14 20 1 0 0 0 0 15 21 1 1 0 0 0 15 23 1 0 0 0 0 16 21 1 0 0 0 0 16 24 2 0 0 0 0 17 20 1 6 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 26 2 0 0 0 0 18 27 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 6 0 0 0 21 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.2
Volume:	382.378
LogP:	0.954
LogD:	0.838
LogS:	-3.195
# Rotatable Bonds:	2
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	6.218
Fsp3:	0.81
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.953
MDCK Permeability:	1.9309982235427015e-05
Pgp-inhibitor:	0.68
Pgp-substrate:	0.321
Human Intestinal Absorption (HIA):	0.3
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.805

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.497
Plasma Protein Binding (PPB):	58.357444763183594%
Volume Distribution (VD):	0.672
Pgp-substrate:	50.17415237426758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.607
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.687
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.147
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	3.263
Half-life (T1/2):	0.593

ADMET: Toxicity

hERG Blockers:	0.312
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.742
Carcinogencity:	0.858
Eye Corrosion:	0.017
Eye Irritation:	0.029
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC470388

Natural Product ID:	NPC470388
*Common Name:**	Methylgeopyxin E
IUPAC Name:	n.a.
Synonyms:	Methylgeopyxin E
Standard InCHIKey:	VGWPXPSFTQHNOH-SNWMAZHOSA-N
Standard InCHI:	InChI=1S/C21H30O6/c1-10-11-5-6-13-20(3)14(7-15(23)21(13,8-11)16(10)24)19(2,18(26)27-4)9-12(22)17(20)25/h11-15,17,22-23,25H,1,5-9H2,2-4H3/t11-,12+,13+,14-,15+,17+,19-,20+,21-/m1/s1
SMILES:	CC1(CC(C(C2(C1CC(C34C2CCC(C3)C(=C)C4=O)O)C)O)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022266
PubChem CID:	57380389
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO33235	geopyxis sp. az0066	Species	Pyronemataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264149]
NPO32738	geopyxis aff. majalis	Species	Pyronemataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264149]

☑ 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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	2270.0	nM	PMID[482363]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	1020.0	nM	PMID[482363]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2080.0	nM	PMID[482363]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	3810.0	nM	PMID[482363]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3990.0	nM	PMID[482363]

☑ 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 NPC470388 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	228
0.1-0.2	1675
0.2-0.3	5512
0.3-0.4	9738
0.4-0.5	11016
0.5-0.6	6046
0.6-0.7	5350
0.7-0.8	2660
0.8-0.85	284
0.85-0.9	120
0.9-0.95	62
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC209298
0.9684	High Similarity	NPC277074
0.9479	High Similarity	NPC122811
0.9468	High Similarity	NPC471038
0.9457	High Similarity	NPC470385
0.9457	High Similarity	NPC470386
0.9388	High Similarity	NPC166993
0.9388	High Similarity	NPC186054
0.9355	High Similarity	NPC470232
0.9293	High Similarity	NPC273155
0.9293	High Similarity	NPC63841
0.9293	High Similarity	NPC231278
0.9293	High Similarity	NPC218123
0.9293	High Similarity	NPC112895
0.9286	High Similarity	NPC138908
0.9286	High Similarity	NPC200957
0.9271	High Similarity	NPC252614
0.9271	High Similarity	NPC46848
0.9255	High Similarity	NPC200054
0.9255	High Similarity	NPC329910
0.9255	High Similarity	NPC29410
0.9255	High Similarity	NPC470387
0.9247	High Similarity	NPC475118
0.9239	High Similarity	NPC211403
0.9239	High Similarity	NPC198242
0.9192	High Similarity	NPC471474
0.9184	High Similarity	NPC301787
0.9175	High Similarity	NPC275990
0.9149	High Similarity	NPC470229
0.9149	High Similarity	NPC98639
0.9109	High Similarity	NPC471093
0.91	High Similarity	NPC469984
0.91	High Similarity	NPC473410
0.91	High Similarity	NPC471094
0.9091	High Similarity	NPC56656
0.9091	High Similarity	NPC222833
0.9082	High Similarity	NPC139347
0.9082	High Similarity	NPC87927
0.9072	High Similarity	NPC289148
0.9072	High Similarity	NPC163963
0.9072	High Similarity	NPC52899
0.9062	High Similarity	NPC89099
0.9062	High Similarity	NPC162459
0.9062	High Similarity	NPC38471
0.9062	High Similarity	NPC20479
0.9062	High Similarity	NPC98837
0.9062	High Similarity	NPC474793
0.9062	High Similarity	NPC38296
0.9062	High Similarity	NPC28864
0.9053	High Similarity	NPC104568
0.9043	High Similarity	NPC47853
0.9032	High Similarity	NPC250753
0.902	High Similarity	NPC29505
0.898	High Similarity	NPC304832
0.898	High Similarity	NPC214946
0.898	High Similarity	NPC286519
0.898	High Similarity	NPC76866
0.898	High Similarity	NPC148628
0.898	High Similarity	NPC246736
0.898	High Similarity	NPC88203
0.8969	High Similarity	NPC127408
0.8969	High Similarity	NPC291785
0.8969	High Similarity	NPC287676
0.8969	High Similarity	NPC267921
0.8969	High Similarity	NPC293866
0.8958	High Similarity	NPC10864
0.8925	High Similarity	NPC80401
0.8922	High Similarity	NPC474786
0.8922	High Similarity	NPC137104
0.8922	High Similarity	NPC85391
0.8922	High Similarity	NPC320383
0.8911	High Similarity	NPC55973
0.89	High Similarity	NPC307660
0.89	High Similarity	NPC130511
0.8889	High Similarity	NPC216114
0.8889	High Similarity	NPC96217
0.8878	High Similarity	NPC148279
0.8878	High Similarity	NPC236585
0.8878	High Similarity	NPC471790
0.8866	High Similarity	NPC78427
0.8866	High Similarity	NPC26270
0.8866	High Similarity	NPC16911
0.8854	High Similarity	NPC256227
0.8854	High Similarity	NPC13949
0.8846	High Similarity	NPC471252
0.8842	High Similarity	NPC191094
0.8842	High Similarity	NPC302008
0.8835	High Similarity	NPC213320
0.883	High Similarity	NPC470230
0.883	High Similarity	NPC476168
0.8824	High Similarity	NPC131903
0.8824	High Similarity	NPC274827
0.8824	High Similarity	NPC102741
0.8812	High Similarity	NPC201908
0.8812	High Similarity	NPC471461
0.8812	High Similarity	NPC67745
0.8812	High Similarity	NPC176949
0.8804	High Similarity	NPC259009
0.8804	High Similarity	NPC153604
0.88	High Similarity	NPC84928
0.88	High Similarity	NPC98603
0.875	High Similarity	NPC474927
0.875	High Similarity	NPC473397
0.875	High Similarity	NPC231060
0.875	High Similarity	NPC41070
0.875	High Similarity	NPC473352
0.875	High Similarity	NPC138245
0.875	High Similarity	NPC84018
0.8738	High Similarity	NPC473324
0.8737	High Similarity	NPC294263
0.8737	High Similarity	NPC181594
0.8737	High Similarity	NPC144739
0.8725	High Similarity	NPC89860
0.8725	High Similarity	NPC189663
0.87	High Similarity	NPC159442
0.8687	High Similarity	NPC14634
0.8667	High Similarity	NPC132668
0.8654	High Similarity	NPC94650
0.8654	High Similarity	NPC122339
0.8646	High Similarity	NPC292374
0.8646	High Similarity	NPC91772
0.8646	High Similarity	NPC129004
0.8646	High Similarity	NPC29247
0.8646	High Similarity	NPC104371
0.8646	High Similarity	NPC111524
0.8646	High Similarity	NPC101233
0.8646	High Similarity	NPC289539
0.8646	High Similarity	NPC153775
0.8646	High Similarity	NPC261333
0.8646	High Similarity	NPC215271
0.8641	High Similarity	NPC118721
0.8641	High Similarity	NPC252679
0.8632	High Similarity	NPC299185
0.8627	High Similarity	NPC88833
0.8627	High Similarity	NPC96333
0.8617	High Similarity	NPC471043
0.8614	High Similarity	NPC474558
0.8614	High Similarity	NPC96268
0.8614	High Similarity	NPC13149
0.8614	High Similarity	NPC202793
0.86	High Similarity	NPC475803
0.86	High Similarity	NPC309388
0.8598	High Similarity	NPC473304
0.8587	High Similarity	NPC190704
0.8587	High Similarity	NPC471034
0.8585	High Similarity	NPC243354
0.8571	High Similarity	NPC471245
0.8571	High Similarity	NPC473303
0.8571	High Similarity	NPC170978
0.8558	High Similarity	NPC471476
0.8558	High Similarity	NPC100908
0.8557	High Similarity	NPC210214
0.8544	High Similarity	NPC232133
0.8544	High Similarity	NPC211224
0.8542	High Similarity	NPC244356
0.8542	High Similarity	NPC224060
0.8542	High Similarity	NPC291373
0.8542	High Similarity	NPC59170
0.8529	High Similarity	NPC37600
0.8529	High Similarity	NPC164600
0.8529	High Similarity	NPC103172
0.8529	High Similarity	NPC295366
0.8526	High Similarity	NPC149761
0.8526	High Similarity	NPC470378
0.8526	High Similarity	NPC261994
0.8526	High Similarity	NPC180849
0.8515	High Similarity	NPC469985
0.8505	High Similarity	NPC88945
0.8505	High Similarity	NPC229752
0.85	High Similarity	NPC71706
0.85	High Similarity	NPC253886
0.85	High Similarity	NPC121218
0.8491	Intermediate Similarity	NPC194273
0.8491	Intermediate Similarity	NPC471248
0.8478	Intermediate Similarity	NPC146683
0.8476	Intermediate Similarity	NPC470281
0.8476	Intermediate Similarity	NPC63244
0.8476	Intermediate Similarity	NPC329953
0.8476	Intermediate Similarity	NPC471243
0.8469	Intermediate Similarity	NPC135548
0.8469	Intermediate Similarity	NPC264979
0.8469	Intermediate Similarity	NPC219353
0.8469	Intermediate Similarity	NPC140242
0.8462	Intermediate Similarity	NPC469983
0.8454	Intermediate Similarity	NPC277399
0.8447	Intermediate Similarity	NPC61071
0.8438	Intermediate Similarity	NPC278106
0.8431	Intermediate Similarity	NPC101842
0.8426	Intermediate Similarity	NPC78836
0.8416	Intermediate Similarity	NPC170615
0.8404	Intermediate Similarity	NPC174619
0.84	Intermediate Similarity	NPC477655
0.84	Intermediate Similarity	NPC180733
0.84	Intermediate Similarity	NPC477656
0.84	Intermediate Similarity	NPC37047
0.84	Intermediate Similarity	NPC94906
0.84	Intermediate Similarity	NPC41971
0.8396	Intermediate Similarity	NPC471244
0.8396	Intermediate Similarity	NPC145625
0.8384	Intermediate Similarity	NPC253586

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 NPC470388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	2114
0.2-0.3	3969
0.3-0.4	1825
0.4-0.5	544
0.5-0.6	229
0.6-0.7	148
0.7-0.8	102
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7982	Intermediate Similarity	NPD4632	Approved
0.7879	Intermediate Similarity	NPD8034	Phase 2
0.7879	Intermediate Similarity	NPD8035	Phase 2
0.7876	Intermediate Similarity	NPD6319	Approved
0.785	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD4634	Approved
0.7611	Intermediate Similarity	NPD6009	Approved
0.7593	Intermediate Similarity	NPD5697	Approved
0.7525	Intermediate Similarity	NPD6079	Approved
0.7523	Intermediate Similarity	NPD6881	Approved
0.7523	Intermediate Similarity	NPD6011	Approved
0.7523	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6008	Approved
0.7477	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7458	Intermediate Similarity	NPD7492	Approved
0.7455	Intermediate Similarity	NPD6372	Approved
0.7455	Intermediate Similarity	NPD6013	Approved
0.7455	Intermediate Similarity	NPD6373	Approved
0.7455	Intermediate Similarity	NPD6012	Approved
0.7455	Intermediate Similarity	NPD6014	Approved
0.7451	Intermediate Similarity	NPD6399	Phase 3
0.7447	Intermediate Similarity	NPD6118	Approved
0.7447	Intermediate Similarity	NPD6697	Approved
0.7447	Intermediate Similarity	NPD6115	Approved
0.7447	Intermediate Similarity	NPD6114	Approved
0.7431	Intermediate Similarity	NPD5701	Approved
0.7429	Intermediate Similarity	NPD7638	Approved
0.7417	Intermediate Similarity	NPD7736	Approved
0.7414	Intermediate Similarity	NPD6054	Approved
0.7411	Intermediate Similarity	NPD8297	Approved
0.7404	Intermediate Similarity	NPD5221	Approved
0.7404	Intermediate Similarity	NPD4697	Phase 3
0.7404	Intermediate Similarity	NPD5222	Approved
0.7404	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6616	Approved
0.7387	Intermediate Similarity	NPD7102	Approved
0.7387	Intermediate Similarity	NPD7290	Approved
0.7387	Intermediate Similarity	NPD6883	Approved
0.7374	Intermediate Similarity	NPD3618	Phase 1
0.7373	Intermediate Similarity	NPD8328	Phase 3
0.7364	Intermediate Similarity	NPD7320	Approved
0.7358	Intermediate Similarity	NPD5286	Approved
0.7358	Intermediate Similarity	NPD5285	Approved
0.7358	Intermediate Similarity	NPD7639	Approved
0.7358	Intermediate Similarity	NPD7640	Approved
0.7358	Intermediate Similarity	NPD4696	Approved
0.7353	Intermediate Similarity	NPD7515	Phase 2
0.735	Intermediate Similarity	NPD5983	Phase 2
0.735	Intermediate Similarity	NPD6016	Approved
0.735	Intermediate Similarity	NPD6015	Approved
0.734	Intermediate Similarity	NPD6116	Phase 1
0.7333	Intermediate Similarity	NPD7902	Approved
0.7333	Intermediate Similarity	NPD5173	Approved
0.7333	Intermediate Similarity	NPD7078	Approved
0.7333	Intermediate Similarity	NPD4755	Approved
0.7321	Intermediate Similarity	NPD6617	Approved
0.7321	Intermediate Similarity	NPD8130	Phase 1
0.7321	Intermediate Similarity	NPD6847	Approved
0.7321	Intermediate Similarity	NPD6869	Approved
0.7312	Intermediate Similarity	NPD3703	Phase 2
0.7304	Intermediate Similarity	NPD7115	Discovery
0.729	Intermediate Similarity	NPD5223	Approved
0.7288	Intermediate Similarity	NPD6370	Approved
0.7288	Intermediate Similarity	NPD5988	Approved
0.7265	Intermediate Similarity	NPD6059	Approved
0.7257	Intermediate Similarity	NPD6882	Approved
0.7245	Intermediate Similarity	NPD4788	Approved
0.7234	Intermediate Similarity	NPD6117	Approved
0.7227	Intermediate Similarity	NPD7604	Phase 2
0.7222	Intermediate Similarity	NPD5226	Approved
0.7222	Intermediate Similarity	NPD5224	Approved
0.7222	Intermediate Similarity	NPD5211	Phase 2
0.7222	Intermediate Similarity	NPD4633	Approved
0.7222	Intermediate Similarity	NPD5225	Approved
0.7213	Intermediate Similarity	NPD7319	Approved
0.7212	Intermediate Similarity	NPD7748	Approved
0.7196	Intermediate Similarity	NPD4700	Approved
0.7193	Intermediate Similarity	NPD8133	Approved
0.719	Intermediate Similarity	NPD8293	Discontinued
0.7168	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5174	Approved
0.7156	Intermediate Similarity	NPD5175	Approved
0.7155	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4202	Approved
0.7107	Intermediate Similarity	NPD7507	Approved
0.7107	Intermediate Similarity	NPD6336	Discontinued
0.7103	Intermediate Similarity	NPD4225	Approved
0.7091	Intermediate Similarity	NPD5141	Approved
0.7069	Intermediate Similarity	NPD6274	Approved
0.7059	Intermediate Similarity	NPD6921	Approved
0.7048	Intermediate Similarity	NPD7900	Approved
0.7048	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6317	Approved
0.7	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD4786	Approved
0.697	Remote Similarity	NPD3667	Approved
0.6964	Remote Similarity	NPD6412	Phase 2
0.6949	Remote Similarity	NPD6335	Approved
0.6949	Remote Similarity	NPD6314	Approved
0.6949	Remote Similarity	NPD6313	Approved
0.693	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6868	Approved
0.6917	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7632	Discontinued
0.6903	Remote Similarity	NPD4730	Approved
0.6903	Remote Similarity	NPD5128	Approved
0.6903	Remote Similarity	NPD4729	Approved
0.6903	Remote Similarity	NPD6686	Approved
0.6891	Remote Similarity	NPD7101	Approved
0.6891	Remote Similarity	NPD7100	Approved
0.6875	Remote Similarity	NPD4768	Approved
0.6875	Remote Similarity	NPD4767	Approved
0.6855	Remote Similarity	NPD6033	Approved
0.6852	Remote Similarity	NPD6083	Phase 2
0.6852	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD3666	Approved
0.6832	Remote Similarity	NPD3133	Approved
0.6832	Remote Similarity	NPD3665	Phase 1
0.6809	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3573	Approved
0.6789	Remote Similarity	NPD5696	Approved
0.6783	Remote Similarity	NPD5251	Approved
0.6783	Remote Similarity	NPD5135	Approved
0.6783	Remote Similarity	NPD5169	Approved
0.6783	Remote Similarity	NPD5248	Approved
0.6783	Remote Similarity	NPD5249	Phase 3
0.6783	Remote Similarity	NPD5247	Approved
0.6783	Remote Similarity	NPD5250	Approved
0.6783	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7525	Registered
0.6754	Remote Similarity	NPD5168	Approved
0.6731	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5737	Approved
0.6731	Remote Similarity	NPD6672	Approved
0.6724	Remote Similarity	NPD5217	Approved
0.6724	Remote Similarity	NPD5216	Approved
0.6724	Remote Similarity	NPD5127	Approved
0.6724	Remote Similarity	NPD5215	Approved
0.6699	Remote Similarity	NPD7334	Approved
0.6699	Remote Similarity	NPD6684	Approved
0.6699	Remote Similarity	NPD5330	Approved
0.6699	Remote Similarity	NPD7146	Approved
0.6699	Remote Similarity	NPD6409	Approved
0.6699	Remote Similarity	NPD7521	Approved
0.6698	Remote Similarity	NPD6411	Approved
0.6698	Remote Similarity	NPD5281	Approved
0.6698	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6333	Approved
0.6641	Remote Similarity	NPD6334	Approved
0.6639	Remote Similarity	NPD6909	Approved
0.6639	Remote Similarity	NPD6908	Approved
0.6637	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4224	Phase 2
0.6612	Remote Similarity	NPD7516	Approved
0.6571	Remote Similarity	NPD6903	Approved
0.6555	Remote Similarity	NPD5167	Approved
0.6538	Remote Similarity	NPD5279	Phase 3
0.6529	Remote Similarity	NPD7327	Approved
0.6529	Remote Similarity	NPD7328	Approved
0.6514	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6101	Approved
0.6505	Remote Similarity	NPD3668	Phase 3
0.6496	Remote Similarity	NPD6371	Approved
0.6481	Remote Similarity	NPD5778	Approved
0.6481	Remote Similarity	NPD5779	Approved
0.6475	Remote Similarity	NPD4522	Approved
0.6471	Remote Similarity	NPD4223	Phase 3
0.6471	Remote Similarity	NPD4221	Approved
0.6458	Remote Similarity	NPD6081	Approved
0.6429	Remote Similarity	NPD3702	Approved
0.6423	Remote Similarity	NPD8294	Approved
0.6423	Remote Similarity	NPD8377	Approved
0.6422	Remote Similarity	NPD6001	Approved
0.6421	Remote Similarity	NPD3698	Phase 2
0.64	Remote Similarity	NPD6067	Discontinued
0.6389	Remote Similarity	NPD7637	Suspended
0.6387	Remote Similarity	NPD6053	Discontinued
0.6371	Remote Similarity	NPD8296	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