NPASS Compound

Structure

CID80326 OpenBabel06191715422D 24 28 0 0 1 0 0 0 0 0999 V2000 2.5970 2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7171 -0.0712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8374 2.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0007 2.9035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1915 -0.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1911 1.4530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5192 0.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8377 1.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3529 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6764 0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8386 2.4195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3527 0.9689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0293 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0291 0.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6763 0.9686 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0002 0.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8383 1.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7179 2.9269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7174 0.9440 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 -5.9503 -0.2980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9499 1.2686 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5146 1.4526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 12 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 17 2 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 7 1 1 0 0 0 11 16 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 9 1 1 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	314.025
LogP:	2.804
LogD:	3.029
LogS:	-5.203
# Rotatable Bonds:	2
TPSA:	55.38
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.844
Synthetic Accessibility Score:	3.422
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.842
MDCK Permeability:	4.552599057205953e-05
Pgp-inhibitor:	0.826
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	94.95343780517578%
Volume Distribution (VD):	0.639
Pgp-substrate:	3.0814712047576904%

ADMET: Metabolism

CYP1A2-inhibitor:	0.519
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.877
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.72
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	6.442
Half-life (T1/2):	0.173

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.43
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.857
Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.88
Skin Sensitization:	0.65
Carcinogencity:	0.739
Eye Corrosion:	0.003
Eye Irritation:	0.148
Respiratory Toxicity:	0.679

Download Data

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

Natural Product: NPC80326

Natural Product ID:	NPC80326
*Common Name:**	FNOOADLKGGWRGC-ZBEGNZNMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FNOOADLKGGWRGC-ZBEGNZNMSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-19-12-4-3-9-16-11(7-21-17(9)18(12)20-2)10-5-14-15(23-8-22-14)6-13(10)24-16/h3-6,11,16H,7-8H2,1-2H3/t11-,16-/m0/s1
SMILES:	COc1ccc2[C@H]3[C@@H](COc2c1OC)c1cc2c(cc1O3)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480288
PubChem CID:	22296258
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO10426	Eysenhardtia polystachya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644061]
NPO6968	Psychotria rostrata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6968	Psychotria rostrata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10426	Eysenhardtia polystachya	Species	Fabaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[512235]

☑ 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 NPC80326 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	547
0.1-0.2	1769
0.2-0.3	4997
0.3-0.4	12244
0.4-0.5	5675
0.5-0.6	4845
0.6-0.7	7929
0.7-0.8	3556
0.8-0.85	846
0.85-0.9	246
0.9-0.95	32
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC300798
0.9925	High Similarity	NPC58137
0.9852	High Similarity	NPC174522
0.9706	High Similarity	NPC472562
0.9638	High Similarity	NPC205316
0.9496	High Similarity	NPC11422
0.9496	High Similarity	NPC42716
0.9496	High Similarity	NPC178014
0.9496	High Similarity	NPC474749
0.9478	High Similarity	NPC474478
0.9433	High Similarity	NPC301961
0.9433	High Similarity	NPC166584
0.9433	High Similarity	NPC71726
0.9429	High Similarity	NPC162193
0.9403	High Similarity	NPC266848
0.9403	High Similarity	NPC136750
0.9338	High Similarity	NPC78047
0.9328	High Similarity	NPC7744
0.9328	High Similarity	NPC72046
0.9328	High Similarity	NPC65183
0.9328	High Similarity	NPC261812
0.9301	High Similarity	NPC238140
0.9291	High Similarity	NPC226540
0.9281	High Similarity	NPC311057
0.9265	High Similarity	NPC189474
0.9254	High Similarity	NPC192255
0.9231	High Similarity	NPC240521
0.922	High Similarity	NPC307466
0.922	High Similarity	NPC180953
0.9214	High Similarity	NPC474808
0.9209	High Similarity	NPC312199
0.9191	High Similarity	NPC31530
0.9191	High Similarity	NPC170779
0.9191	High Similarity	NPC90083
0.9178	High Similarity	NPC159922
0.9137	High Similarity	NPC27495
0.9137	High Similarity	NPC216434
0.9137	High Similarity	NPC103448
0.9124	High Similarity	NPC49235
0.9124	High Similarity	NPC148893
0.9124	High Similarity	NPC25333
0.9065	High Similarity	NPC292487
0.9065	High Similarity	NPC9068
0.9058	High Similarity	NPC121651
0.9037	High Similarity	NPC237169
0.9037	High Similarity	NPC470624
0.903	High Similarity	NPC158471
0.903	High Similarity	NPC57119
0.903	High Similarity	NPC222127
0.903	High Similarity	NPC226862
0.903	High Similarity	NPC31707
0.903	High Similarity	NPC82862
0.903	High Similarity	NPC165128
0.9028	High Similarity	NPC270751
0.9007	High Similarity	NPC474295
0.9007	High Similarity	NPC107161
0.9	High Similarity	NPC226547
0.8993	High Similarity	NPC185908
0.8993	High Similarity	NPC196420
0.8986	High Similarity	NPC474139
0.8971	High Similarity	NPC227160
0.8971	High Similarity	NPC82111
0.8966	High Similarity	NPC286235
0.8966	High Similarity	NPC55158
0.8966	High Similarity	NPC51328
0.8955	High Similarity	NPC473093
0.8955	High Similarity	NPC8050
0.8955	High Similarity	NPC473092
0.8944	High Similarity	NPC81638
0.8936	High Similarity	NPC247291
0.8929	High Similarity	NPC471388
0.8929	High Similarity	NPC113550
0.8921	High Similarity	NPC173660
0.8921	High Similarity	NPC197166
0.8921	High Similarity	NPC11453
0.8921	High Similarity	NPC32189
0.8897	High Similarity	NPC175976
0.8897	High Similarity	NPC248132
0.8897	High Similarity	NPC130449
0.8897	High Similarity	NPC233224
0.8897	High Similarity	NPC271208
0.8889	High Similarity	NPC328682
0.8889	High Similarity	NPC281864
0.8889	High Similarity	NPC33832
0.8889	High Similarity	NPC54321
0.8881	High Similarity	NPC45257
0.8881	High Similarity	NPC112571
0.8881	High Similarity	NPC50683
0.8881	High Similarity	NPC93323
0.8881	High Similarity	NPC280092
0.8881	High Similarity	NPC12641
0.8881	High Similarity	NPC285725
0.8873	High Similarity	NPC246947
0.8865	High Similarity	NPC309124
0.8865	High Similarity	NPC46591
0.8865	High Similarity	NPC254759
0.8865	High Similarity	NPC160283
0.8865	High Similarity	NPC184797
0.8865	High Similarity	NPC177868
0.8865	High Similarity	NPC284464
0.8857	High Similarity	NPC283949
0.8849	High Similarity	NPC195022
0.8849	High Similarity	NPC150534
0.8841	High Similarity	NPC196937
0.8841	High Similarity	NPC1474
0.8836	High Similarity	NPC95392
0.8836	High Similarity	NPC35877
0.8836	High Similarity	NPC55715
0.8832	High Similarity	NPC473412
0.8832	High Similarity	NPC469698
0.8828	High Similarity	NPC116019
0.8828	High Similarity	NPC227902
0.8828	High Similarity	NPC39657
0.8811	High Similarity	NPC298317
0.8811	High Similarity	NPC47633
0.8811	High Similarity	NPC102044
0.8811	High Similarity	NPC85264
0.8811	High Similarity	NPC255566
0.8803	High Similarity	NPC471389
0.8794	High Similarity	NPC292882
0.8794	High Similarity	NPC236306
0.8794	High Similarity	NPC473739
0.8794	High Similarity	NPC30951
0.8794	High Similarity	NPC127218
0.8794	High Similarity	NPC245207
0.8794	High Similarity	NPC319647
0.8794	High Similarity	NPC6369
0.8794	High Similarity	NPC232164
0.8794	High Similarity	NPC25966
0.8786	High Similarity	NPC143895
0.8786	High Similarity	NPC172818
0.8786	High Similarity	NPC25695
0.8784	High Similarity	NPC302610
0.8777	High Similarity	NPC145722
0.8777	High Similarity	NPC256776
0.8777	High Similarity	NPC185680
0.8776	High Similarity	NPC472710
0.8776	High Similarity	NPC472709
0.8768	High Similarity	NPC100223
0.8768	High Similarity	NPC171928
0.8768	High Similarity	NPC158526
0.8768	High Similarity	NPC16830
0.8768	High Similarity	NPC129687
0.8768	High Similarity	NPC33611
0.8759	High Similarity	NPC99515
0.8759	High Similarity	NPC190714
0.875	High Similarity	NPC172171
0.875	High Similarity	NPC79429
0.875	High Similarity	NPC239254
0.875	High Similarity	NPC471667
0.875	High Similarity	NPC63879
0.875	High Similarity	NPC217635
0.8741	High Similarity	NPC9891
0.8741	High Similarity	NPC186845
0.8741	High Similarity	NPC287124
0.8741	High Similarity	NPC88297
0.8733	High Similarity	NPC164152
0.8732	High Similarity	NPC56091
0.8731	High Similarity	NPC34902
0.8731	High Similarity	NPC18449
0.8731	High Similarity	NPC191768
0.8731	High Similarity	NPC92869
0.8731	High Similarity	NPC283170
0.8731	High Similarity	NPC294156
0.8731	High Similarity	NPC256015
0.8731	High Similarity	NPC121783
0.8723	High Similarity	NPC477938
0.8723	High Similarity	NPC474282
0.8723	High Similarity	NPC107551
0.8723	High Similarity	NPC326797
0.8723	High Similarity	NPC276490
0.8723	High Similarity	NPC102904
0.8723	High Similarity	NPC176051
0.8723	High Similarity	NPC103976
0.8716	High Similarity	NPC474975
0.8714	High Similarity	NPC224941
0.8714	High Similarity	NPC311430
0.8705	High Similarity	NPC58585
0.8705	High Similarity	NPC263064
0.8699	High Similarity	NPC16269
0.8699	High Similarity	NPC21776
0.869	High Similarity	NPC22150
0.869	High Similarity	NPC475868
0.869	High Similarity	NPC475096
0.869	High Similarity	NPC38041
0.869	High Similarity	NPC43508
0.869	High Similarity	NPC476301
0.869	High Similarity	NPC279298
0.8681	High Similarity	NPC218510
0.8681	High Similarity	NPC252169
0.8681	High Similarity	NPC76415
0.8681	High Similarity	NPC12728
0.8681	High Similarity	NPC477616
0.8681	High Similarity	NPC185071
0.8676	High Similarity	NPC98745
0.8675	High Similarity	NPC189730
0.8671	High Similarity	NPC311530
0.8671	High Similarity	NPC108674
0.8662	High Similarity	NPC156376
0.8652	High Similarity	NPC265433

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 NPC80326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	435
0.1-0.2	915
0.2-0.3	1991
0.3-0.4	2715
0.4-0.5	1606
0.5-0.6	872
0.6-0.7	536
0.7-0.8	73
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8239	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1613	Approved
0.8235	Intermediate Similarity	NPD3705	Approved
0.8194	Intermediate Similarity	NPD4965	Approved
0.8194	Intermediate Similarity	NPD4966	Approved
0.8194	Intermediate Similarity	NPD4967	Phase 2
0.8101	Intermediate Similarity	NPD7199	Phase 2
0.8089	Intermediate Similarity	NPD6234	Discontinued
0.8085	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5494	Approved
0.8028	Intermediate Similarity	NPD3027	Phase 3
0.8014	Intermediate Similarity	NPD2861	Phase 2
0.8014	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1653	Approved
0.7958	Intermediate Similarity	NPD4908	Phase 1
0.7919	Intermediate Similarity	NPD6674	Discontinued
0.7853	Intermediate Similarity	NPD7228	Approved
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1610	Phase 2
0.7836	Intermediate Similarity	NPD5283	Phase 1
0.7771	Intermediate Similarity	NPD3382	Approved
0.7771	Intermediate Similarity	NPD3384	Approved
0.7771	Intermediate Similarity	NPD3383	Approved
0.7762	Intermediate Similarity	NPD3018	Phase 2
0.7677	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7240	Approved
0.766	Intermediate Similarity	NPD2981	Phase 2
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.7613	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2982	Phase 2
0.7606	Intermediate Similarity	NPD2983	Phase 2
0.7589	Intermediate Similarity	NPD1091	Approved
0.7547	Intermediate Similarity	NPD1934	Approved
0.7545	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD7054	Approved
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7484	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4749	Approved
0.7468	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7472	Approved
0.7429	Intermediate Similarity	NPD1548	Phase 1
0.7419	Intermediate Similarity	NPD5058	Phase 3
0.7417	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4625	Phase 3
0.7412	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7466	Approved
0.7391	Intermediate Similarity	NPD2801	Approved
0.7391	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1357	Approved
0.7368	Intermediate Similarity	NPD3454	Phase 3
0.7365	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3817	Phase 2
0.7338	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1375	Discontinued
0.731	Intermediate Similarity	NPD7549	Discontinued
0.731	Intermediate Similarity	NPD7808	Phase 3
0.7301	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6797	Phase 2
0.7256	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3539	Phase 1
0.7251	Intermediate Similarity	NPD7251	Discontinued
0.7251	Intermediate Similarity	NPD6559	Discontinued
0.7248	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3540	Phase 1
0.7208	Intermediate Similarity	NPD7266	Discontinued
0.7202	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6166	Phase 2
0.7197	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7124	Phase 2
0.7195	Intermediate Similarity	NPD3882	Suspended
0.7186	Intermediate Similarity	NPD3787	Discontinued
0.7184	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD2796	Approved
0.7126	Intermediate Similarity	NPD1247	Approved
0.7126	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5327	Phase 3
0.7115	Intermediate Similarity	NPD1652	Phase 2
0.7105	Intermediate Similarity	NPD6355	Discontinued
0.7105	Intermediate Similarity	NPD5124	Phase 1
0.7105	Intermediate Similarity	NPD1933	Approved
0.7105	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6671	Approved
0.7081	Intermediate Similarity	NPD4210	Discontinued
0.7078	Intermediate Similarity	NPD5588	Approved
0.7078	Intermediate Similarity	NPD4108	Discontinued
0.7075	Intermediate Similarity	NPD8651	Approved
0.7073	Intermediate Similarity	NPD8455	Phase 2
0.707	Intermediate Similarity	NPD3892	Phase 2
0.707	Intermediate Similarity	NPD4110	Phase 3
0.707	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6331	Phase 2
0.7041	Intermediate Similarity	NPD3926	Phase 2
0.7033	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4538	Approved
0.7013	Intermediate Similarity	NPD6111	Discontinued
0.7013	Intermediate Similarity	NPD7097	Phase 1
0.7013	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4536	Approved
0.7011	Intermediate Similarity	NPD5006	Approved
0.7011	Intermediate Similarity	NPD5005	Approved
0.7006	Intermediate Similarity	NPD919	Approved
0.7006	Intermediate Similarity	NPD5177	Phase 3
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5535	Approved
0.7	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4481	Phase 3
0.6994	Remote Similarity	NPD4675	Approved
0.6994	Remote Similarity	NPD4678	Approved
0.6993	Remote Similarity	NPD5735	Approved
0.6993	Remote Similarity	NPD5536	Phase 2
0.6993	Remote Similarity	NPD3657	Discovery
0.6987	Remote Similarity	NPD5762	Approved
0.6987	Remote Similarity	NPD5763	Approved
0.6986	Remote Similarity	NPD1611	Approved
0.6982	Remote Similarity	NPD7229	Phase 3
0.698	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8156	Discontinued
0.6974	Remote Similarity	NPD6233	Phase 2
0.6973	Remote Similarity	NPD7680	Approved
0.6972	Remote Similarity	NPD7157	Approved
0.697	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7819	Suspended
0.6968	Remote Similarity	NPD3748	Approved
0.6966	Remote Similarity	NPD5125	Phase 3
0.6966	Remote Similarity	NPD5126	Approved
0.6964	Remote Similarity	NPD5677	Discontinued
0.6962	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2684	Approved
0.6951	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1511	Approved
0.6937	Remote Similarity	NPD7212	Phase 2
0.6937	Remote Similarity	NPD7213	Phase 3
0.6933	Remote Similarity	NPD4005	Discontinued
0.6928	Remote Similarity	NPD3620	Phase 2
0.6928	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5402	Approved
0.6923	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD2161	Phase 2
0.6923	Remote Similarity	NPD6099	Approved
0.6919	Remote Similarity	NPD3751	Discontinued
0.6919	Remote Similarity	NPD8252	Approved
0.6919	Remote Similarity	NPD8099	Discontinued
0.6919	Remote Similarity	NPD8251	Approved
0.6918	Remote Similarity	NPD3496	Discontinued
0.6914	Remote Similarity	NPD5976	Discontinued
0.691	Remote Similarity	NPD6843	Phase 3
0.691	Remote Similarity	NPD6842	Approved
0.691	Remote Similarity	NPD6841	Approved
0.6908	Remote Similarity	NPD5111	Phase 2
0.6908	Remote Similarity	NPD5110	Phase 2
0.6908	Remote Similarity	NPD6798	Discontinued
0.6908	Remote Similarity	NPD5109	Approved
0.6903	Remote Similarity	NPD2200	Suspended
0.6903	Remote Similarity	NPD7119	Phase 2
0.6899	Remote Similarity	NPD4236	Phase 3
0.6899	Remote Similarity	NPD4237	Approved
0.6897	Remote Similarity	NPD5585	Approved
0.6894	Remote Similarity	NPD7447	Phase 1
0.689	Remote Similarity	NPD7028	Phase 2
0.6885	Remote Similarity	NPD4420	Approved
0.6882	Remote Similarity	NPD6232	Discontinued
0.6882	Remote Similarity	NPD3051	Approved
0.6879	Remote Similarity	NPD7843	Approved
0.6879	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD422	Phase 1
0.6867	Remote Similarity	NPD1465	Phase 2
0.6867	Remote Similarity	NPD2978	Approved
0.6867	Remote Similarity	NPD2977	Approved
0.6863	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7473	Discontinued
0.6859	Remote Similarity	NPD5960	Phase 3
0.6855	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1512	Approved
0.6849	Remote Similarity	NPD17	Approved
0.6846	Remote Similarity	NPD6696	Suspended
0.6845	Remote Similarity	NPD7075	Discontinued
0.6842	Remote Similarity	NPD2969	Approved
0.6842	Remote Similarity	NPD7095	Approved
0.6842	Remote Similarity	NPD2970	Approved
0.6835	Remote Similarity	NPD1549	Phase 2
0.6835	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6799	Approved
0.6829	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2560	Approved
0.6826	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2563	Approved
0.6824	Remote Similarity	NPD8127	Discontinued

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