NPASS Compound

Structure

CID90185 OpenBabel06191715422D 22 25 0 0 0 0 0 0 0 0999 V2000 -3.3712 3.1492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1713 -1.0547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0697 0.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0696 1.4099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2558 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2556 1.8797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6280 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.8195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4418 0.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4417 1.4097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8138 0.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8139 3.2894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8141 1.4096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6279 1.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6278 2.8193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8138 1.4096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8140 4.2654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7534 1.6614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4418 3.2893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2432 -0.9077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 2 0 0 0 0 6 10 2 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	295.08
Volume:	293.428
LogP:	3.744
LogD:	2.992
LogS:	-6.812
# Rotatable Bonds:	2
TPSA:	59.0
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	2.758
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.784
MDCK Permeability:	1.8118707885150798e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.193
Plasma Protein Binding (PPB):	93.13320922851562%
Volume Distribution (VD):	0.477
Pgp-substrate:	8.249300956726074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.234
CYP2C19-substrate:	0.545
CYP2C9-inhibitor:	0.603
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.583
CYP2D6-substrate:	0.489
CYP3A4-inhibitor:	0.52
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	1.397
Half-life (T1/2):	0.215

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.596
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.846
Rat Oral Acute Toxicity:	0.324
Maximum Recommended Daily Dose:	0.699
Skin Sensitization:	0.723
Carcinogencity:	0.94
Eye Corrosion:	0.012
Eye Irritation:	0.608
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC90185

Natural Product ID:	NPC90185
*Common Name:**	Piperlactam S
IUPAC Name:	n.a.
Synonyms:	Piperlactam S
Standard InCHIKey:	LHSDJNRAZBFFLF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H13NO4/c1-21-16-13(19)8-11-14-12(18(22-2)17(11)20)7-9-5-3-4-6-10(9)15(14)16/h3-8,19H,1-2H3
SMILES:	COc1c(O)cc2c3c1c1ccccc1cc3n(c2=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497039
PubChem CID:	622222
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002663] Aristolactams

*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
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11040054]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724856]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19900811]
NPO9925	Rhododendron latoucheae	Species	Ericaceae	Eukaryota	Twigs; Leaves	n.a.	n.a.	PMID[30106288]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8368081]
NPO9480	Huperzia miyoshiana	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9480	Huperzia miyoshiana	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7522	Streptomyces amakusaensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO313	Castilleja sulphurea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9571	Pseudobrickellia brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9301	Dioscorea sativa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9925	Rhododendron latoucheae	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19174	Anoplophora chinensis	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9480	Huperzia miyoshiana	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1155	Forsythia japonica	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6475	Gymnosporia trigyna	Species	Celastraceae	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7000.0	nM	PMID[468699]

☑ 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 NPC90185 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	460
0.1-0.2	2351
0.2-0.3	8758
0.3-0.4	8415
0.4-0.5	6011
0.5-0.6	12758
0.6-0.7	3772
0.7-0.8	151
0.8-0.85	13
0.85-0.9	4
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9574	High Similarity	NPC100573
0.9574	High Similarity	NPC207873
0.9082	High Similarity	NPC298449
0.8724	High Similarity	NPC308943
0.8724	High Similarity	NPC222561
0.8607	High Similarity	NPC55470
0.8507	High Similarity	NPC91234
0.845	Intermediate Similarity	NPC121510
0.845	Intermediate Similarity	NPC85661
0.845	Intermediate Similarity	NPC171882
0.84	Intermediate Similarity	NPC46679
0.8316	Intermediate Similarity	NPC17677
0.825	Intermediate Similarity	NPC38961
0.8204	Intermediate Similarity	NPC240684
0.8177	Intermediate Similarity	NPC276674
0.8177	Intermediate Similarity	NPC33902
0.8155	Intermediate Similarity	NPC290227
0.81	Intermediate Similarity	NPC471489
0.8093	Intermediate Similarity	NPC320088
0.802	Intermediate Similarity	NPC254957
0.801	Intermediate Similarity	NPC61731
0.801	Intermediate Similarity	NPC186569
0.8	Intermediate Similarity	NPC5374
0.795	Intermediate Similarity	NPC71124
0.7933	Intermediate Similarity	NPC124658
0.7933	Intermediate Similarity	NPC227361
0.7931	Intermediate Similarity	NPC207971
0.7868	Intermediate Similarity	NPC474904
0.7861	Intermediate Similarity	NPC23080
0.7861	Intermediate Similarity	NPC193906
0.7812	Intermediate Similarity	NPC285941
0.7805	Intermediate Similarity	NPC268077
0.7755	Intermediate Similarity	NPC28425
0.7755	Intermediate Similarity	NPC249405
0.7746	Intermediate Similarity	NPC256422
0.7744	Intermediate Similarity	NPC311936
0.7704	Intermediate Similarity	NPC119579
0.7692	Intermediate Similarity	NPC190461
0.7653	Intermediate Similarity	NPC192939
0.7653	Intermediate Similarity	NPC215747
0.7619	Intermediate Similarity	NPC25961
0.7602	Intermediate Similarity	NPC260118
0.76	Intermediate Similarity	NPC312531
0.7583	Intermediate Similarity	NPC295479
0.7583	Intermediate Similarity	NPC220241
0.7574	Intermediate Similarity	NPC78284
0.7551	Intermediate Similarity	NPC265383
0.755	Intermediate Similarity	NPC22928
0.7547	Intermediate Similarity	NPC470481
0.7547	Intermediate Similarity	NPC470482
0.7534	Intermediate Similarity	NPC285254
0.7525	Intermediate Similarity	NPC179704
0.75	Intermediate Similarity	NPC162653
0.75	Intermediate Similarity	NPC180253
0.75	Intermediate Similarity	NPC219170
0.7477	Intermediate Similarity	NPC251071
0.7462	Intermediate Similarity	NPC287588
0.744	Intermediate Similarity	NPC25897
0.7426	Intermediate Similarity	NPC112676
0.7426	Intermediate Similarity	NPC296742
0.74	Intermediate Similarity	NPC276060
0.738	Intermediate Similarity	NPC15406
0.7376	Intermediate Similarity	NPC224293
0.7376	Intermediate Similarity	NPC477186
0.7374	Intermediate Similarity	NPC5167
0.7373	Intermediate Similarity	NPC182853
0.7353	Intermediate Similarity	NPC294244
0.7352	Intermediate Similarity	NPC7560
0.7344	Intermediate Similarity	NPC135006
0.7343	Intermediate Similarity	NPC293624
0.7327	Intermediate Similarity	NPC69213
0.73	Intermediate Similarity	NPC99723
0.7295	Intermediate Similarity	NPC24228
0.7294	Intermediate Similarity	NPC134702
0.7293	Intermediate Similarity	NPC210296
0.7286	Intermediate Similarity	NPC85613
0.7268	Intermediate Similarity	NPC196231
0.7265	Intermediate Similarity	NPC77878
0.7257	Intermediate Similarity	NPC22481
0.7254	Intermediate Similarity	NPC27410
0.7254	Intermediate Similarity	NPC166014
0.7248	Intermediate Similarity	NPC126556
0.724	Intermediate Similarity	NPC210434
0.7233	Intermediate Similarity	NPC302001
0.7225	Intermediate Similarity	NPC212163
0.7222	Intermediate Similarity	NPC116178
0.7202	Intermediate Similarity	NPC213401
0.72	Intermediate Similarity	NPC24019
0.72	Intermediate Similarity	NPC283810
0.7198	Intermediate Similarity	NPC29472
0.7197	Intermediate Similarity	NPC89549
0.7195	Intermediate Similarity	NPC118189
0.7191	Intermediate Similarity	NPC183537
0.7189	Intermediate Similarity	NPC114468
0.7189	Intermediate Similarity	NPC217903
0.7188	Intermediate Similarity	NPC470480
0.7181	Intermediate Similarity	NPC39361
0.7179	Intermediate Similarity	NPC324144
0.7173	Intermediate Similarity	NPC306011
0.7173	Intermediate Similarity	NPC472838
0.7163	Intermediate Similarity	NPC46990
0.7162	Intermediate Similarity	NPC182907
0.7162	Intermediate Similarity	NPC189903
0.7158	Intermediate Similarity	NPC261322
0.7157	Intermediate Similarity	NPC117188
0.7157	Intermediate Similarity	NPC205421
0.7157	Intermediate Similarity	NPC306555
0.7157	Intermediate Similarity	NPC81218
0.7157	Intermediate Similarity	NPC158376
0.7157	Intermediate Similarity	NPC474931
0.7157	Intermediate Similarity	NPC12053
0.7157	Intermediate Similarity	NPC145832
0.7156	Intermediate Similarity	NPC2905
0.7156	Intermediate Similarity	NPC295676
0.7143	Intermediate Similarity	NPC136508
0.7143	Intermediate Similarity	NPC13504
0.7143	Intermediate Similarity	NPC207239
0.7143	Intermediate Similarity	NPC253043
0.7143	Intermediate Similarity	NPC10732
0.7143	Intermediate Similarity	NPC96603
0.7143	Intermediate Similarity	NPC116284
0.7143	Intermediate Similarity	NPC306843
0.7143	Intermediate Similarity	NPC78222
0.7143	Intermediate Similarity	NPC212794
0.7143	Intermediate Similarity	NPC477563
0.7143	Intermediate Similarity	NPC196447
0.7143	Intermediate Similarity	NPC119722
0.7136	Intermediate Similarity	NPC82056
0.7128	Intermediate Similarity	NPC153631
0.7128	Intermediate Similarity	NPC24954
0.7124	Intermediate Similarity	NPC278525
0.7118	Intermediate Similarity	NPC108342
0.7117	Intermediate Similarity	NPC76478
0.711	Intermediate Similarity	NPC321166
0.7108	Intermediate Similarity	NPC116007
0.7107	Intermediate Similarity	NPC81247
0.7107	Intermediate Similarity	NPC35627
0.7107	Intermediate Similarity	NPC476573
0.7107	Intermediate Similarity	NPC132385
0.7106	Intermediate Similarity	NPC270515
0.7101	Intermediate Similarity	NPC79213
0.7098	Intermediate Similarity	NPC186063
0.7094	Intermediate Similarity	NPC298339
0.7091	Intermediate Similarity	NPC313327
0.7083	Intermediate Similarity	NPC118427
0.7083	Intermediate Similarity	NPC302783
0.7083	Intermediate Similarity	NPC473201
0.708	Intermediate Similarity	NPC315914
0.7079	Intermediate Similarity	NPC114364
0.7079	Intermediate Similarity	NPC320223
0.7078	Intermediate Similarity	NPC148391
0.7077	Intermediate Similarity	NPC167098
0.7077	Intermediate Similarity	NPC296044
0.7074	Intermediate Similarity	NPC91694
0.7074	Intermediate Similarity	NPC476220
0.7074	Intermediate Similarity	NPC160113
0.7074	Intermediate Similarity	NPC253675
0.7074	Intermediate Similarity	NPC300603
0.7071	Intermediate Similarity	NPC298979
0.7071	Intermediate Similarity	NPC471604
0.7071	Intermediate Similarity	NPC210140
0.707	Intermediate Similarity	NPC198160
0.7069	Intermediate Similarity	NPC475844
0.7065	Intermediate Similarity	NPC229166
0.7065	Intermediate Similarity	NPC199465
0.7065	Intermediate Similarity	NPC128560
0.7059	Intermediate Similarity	NPC229218
0.7059	Intermediate Similarity	NPC169214
0.7059	Intermediate Similarity	NPC192597
0.7059	Intermediate Similarity	NPC141817
0.7059	Intermediate Similarity	NPC176030
0.7056	Intermediate Similarity	NPC244606
0.7056	Intermediate Similarity	NPC156728
0.7054	Intermediate Similarity	NPC94842
0.7053	Intermediate Similarity	NPC58373
0.7051	Intermediate Similarity	NPC474366
0.7051	Intermediate Similarity	NPC269449
0.705	Intermediate Similarity	NPC67978
0.705	Intermediate Similarity	NPC303581
0.7047	Intermediate Similarity	NPC164912
0.7045	Intermediate Similarity	NPC38964
0.7043	Intermediate Similarity	NPC154922
0.7041	Intermediate Similarity	NPC60186
0.7039	Intermediate Similarity	NPC162694
0.7037	Intermediate Similarity	NPC160777
0.7037	Intermediate Similarity	NPC73416
0.7035	Intermediate Similarity	NPC13249
0.7035	Intermediate Similarity	NPC241055
0.7031	Intermediate Similarity	NPC295977
0.7031	Intermediate Similarity	NPC58310
0.703	Intermediate Similarity	NPC222524
0.7026	Intermediate Similarity	NPC288353
0.7026	Intermediate Similarity	NPC109765
0.7024	Intermediate Similarity	NPC83511
0.7023	Intermediate Similarity	NPC261388
0.7015	Intermediate Similarity	NPC66341
0.7015	Intermediate Similarity	NPC477020
0.7015	Intermediate Similarity	NPC192135
0.7013	Intermediate Similarity	NPC6786
0.7009	Intermediate Similarity	NPC159101

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 NPC90185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	801
0.2-0.3	954
0.3-0.4	1803
0.4-0.5	2812
0.5-0.6	1957
0.6-0.7	480
0.7-0.8	19
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.79	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD7922	Phase 1
0.7453	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8149	Discontinued
0.7427	Intermediate Similarity	NPD5071	Phase 2
0.7358	Intermediate Similarity	NPD4859	Phase 1
0.7306	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6723	Discontinued
0.7255	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5025	Approved
0.7183	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD824	Approved
0.7143	Intermediate Similarity	NPD6457	Approved
0.7143	Intermediate Similarity	NPD7225	Discontinued
0.713	Intermediate Similarity	NPD7278	Phase 2
0.713	Intermediate Similarity	NPD7279	Phase 2
0.7116	Intermediate Similarity	NPD5950	Discontinued
0.7107	Intermediate Similarity	NPD5186	Approved
0.7107	Intermediate Similarity	NPD5183	Approved
0.7104	Intermediate Similarity	NPD2899	Discontinued
0.71	Intermediate Similarity	NPD1221	Approved
0.7094	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6997	Phase 2
0.7056	Intermediate Similarity	NPD2821	Approved
0.7042	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD710	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD7654	Discontinued
0.6996	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD3229	Phase 2
0.6971	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1220	Phase 1
0.6915	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7324	Discontinued
0.6897	Remote Similarity	NPD7479	Phase 2
0.689	Remote Similarity	NPD2488	Approved
0.689	Remote Similarity	NPD2490	Approved
0.6888	Remote Similarity	NPD5977	Approved
0.6888	Remote Similarity	NPD5978	Approved
0.6884	Remote Similarity	NPD2491	Approved
0.6884	Remote Similarity	NPD3448	Approved
0.6869	Remote Similarity	NPD3289	Phase 3
0.6869	Remote Similarity	NPD3290	Approved
0.6867	Remote Similarity	NPD4846	Phase 2
0.6866	Remote Similarity	NPD2898	Approved
0.6863	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD3437	Discontinued
0.6842	Remote Similarity	NPD5928	Phase 1
0.6837	Remote Similarity	NPD6321	Discontinued
0.6831	Remote Similarity	NPD8091	Phase 3
0.6829	Remote Similarity	NPD5637	Discontinued
0.6822	Remote Similarity	NPD6716	Phase 1
0.6818	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD6161	Approved
0.6808	Remote Similarity	NPD5564	Approved
0.6808	Remote Similarity	NPD6162	Approved
0.6806	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3057	Approved
0.6804	Remote Similarity	NPD5086	Approved
0.6798	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7177	Discontinued
0.6794	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3398	Discontinued
0.6776	Remote Similarity	NPD5196	Approved
0.6776	Remote Similarity	NPD5194	Approved
0.6776	Remote Similarity	NPD5197	Approved
0.6763	Remote Similarity	NPD7546	Discontinued
0.6762	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2493	Approved
0.6759	Remote Similarity	NPD3450	Approved
0.6759	Remote Similarity	NPD3452	Approved
0.6759	Remote Similarity	NPD2494	Approved
0.6758	Remote Similarity	NPD7263	Phase 2
0.6758	Remote Similarity	NPD6296	Discontinued
0.6754	Remote Similarity	NPD3912	Discontinued
0.6753	Remote Similarity	NPD4981	Phase 2
0.6749	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD7262	Phase 1
0.6741	Remote Similarity	NPD7047	Phase 3
0.6736	Remote Similarity	NPD5488	Discontinued
0.6728	Remote Similarity	NPD2972	Approved
0.6728	Remote Similarity	NPD3533	Approved
0.6726	Remote Similarity	NPD3258	Approved
0.6723	Remote Similarity	NPD7048	Phase 3
0.6713	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD683	Approved
0.671	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3252	Approved
0.6698	Remote Similarity	NPD4668	Phase 2
0.6683	Remote Similarity	NPD3793	Phase 3
0.6683	Remote Similarity	NPD6232	Discontinued
0.6682	Remote Similarity	NPD7301	Phase 3
0.6681	Remote Similarity	NPD7395	Discontinued
0.6667	Remote Similarity	NPD4466	Phase 1
0.6667	Remote Similarity	NPD4582	Approved
0.6667	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD6181	Discontinued
0.6667	Remote Similarity	NPD4328	Approved
0.6667	Remote Similarity	NPD5610	Approved
0.6667	Remote Similarity	NPD4583	Approved
0.6667	Remote Similarity	NPD6874	Approved
0.6667	Remote Similarity	NPD5914	Approved
0.6652	Remote Similarity	NPD6962	Phase 2
0.6652	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8067	Phase 3
0.6651	Remote Similarity	NPD5195	Discontinued
0.6651	Remote Similarity	NPD7626	Approved
0.6651	Remote Similarity	NPD7627	Approved
0.6651	Remote Similarity	NPD5641	Discontinued
0.6651	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4083	Discontinued
0.6635	Remote Similarity	NPD7291	Discontinued
0.6632	Remote Similarity	NPD2420	Approved
0.6632	Remote Similarity	NPD2421	Approved
0.6622	Remote Similarity	NPD3257	Approved
0.6622	Remote Similarity	NPD7559	Phase 2
0.6621	Remote Similarity	NPD4004	Approved
0.6621	Remote Similarity	NPD4002	Approved
0.6618	Remote Similarity	NPD5445	Approved
0.6617	Remote Similarity	NPD5430	Discontinued
0.6615	Remote Similarity	NPD1670	Discontinued
0.661	Remote Similarity	NPD3752	Phase 2
0.6605	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7280	Phase 3
0.6603	Remote Similarity	NPD7281	Phase 3
0.6602	Remote Similarity	NPD5810	Discontinued
0.6599	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3298	Approved
0.6591	Remote Similarity	NPD1294	Discontinued
0.659	Remote Similarity	NPD5608	Approved
0.659	Remote Similarity	NPD5609	Approved
0.6589	Remote Similarity	NPD4539	Phase 1
0.6585	Remote Similarity	NPD7473	Discontinued
0.6579	Remote Similarity	NPD4111	Phase 1
0.6579	Remote Similarity	NPD4665	Approved
0.6579	Remote Similarity	NPD5496	Approved
0.6578	Remote Similarity	NPD4356	Discontinued
0.6575	Remote Similarity	NPD7316	Discontinued
0.6574	Remote Similarity	NPD2975	Approved
0.6574	Remote Similarity	NPD2973	Approved
0.6574	Remote Similarity	NPD2974	Approved
0.6573	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3920	Phase 2
0.6569	Remote Similarity	NPD7417	Discontinued
0.6569	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6719	Approved
0.6562	Remote Similarity	NPD5676	Approved
0.656	Remote Similarity	NPD4107	Approved
0.6557	Remote Similarity	NPD7693	Approved
0.6555	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6517	Phase 3
0.6542	Remote Similarity	NPD5937	Approved
0.6538	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6297	Approved
0.6538	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD6894	Phase 1
0.6537	Remote Similarity	NPD2489	Approved
0.6537	Remote Similarity	NPD27	Approved
0.6532	Remote Similarity	NPD5429	Discontinued
0.6531	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.653	Remote Similarity	NPD6238	Discontinued
0.6528	Remote Similarity	NPD5582	Discontinued
0.6528	Remote Similarity	NPD3301	Approved
0.6527	Remote Similarity	NPD8016	Phase 3
0.6527	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4373	Phase 2
0.6524	Remote Similarity	NPD2968	Approved
0.6524	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2971	Approved
0.6522	Remote Similarity	NPD6020	Phase 2
0.652	Remote Similarity	NPD6747	Phase 1
0.652	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4040	Phase 1
0.6513	Remote Similarity	NPD5805	Approved
0.6507	Remote Similarity	NPD3763	Approved
0.6505	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7302	Phase 3
0.6502	Remote Similarity	NPD7300	Phase 3
0.6502	Remote Similarity	NPD3251	Approved
0.6502	Remote Similarity	NPD5823	Approved
0.6498	Remote Similarity	NPD5515	Phase 2
0.6495	Remote Similarity	NPD3141	Discontinued
0.6494	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6618	Phase 2
0.6491	Remote Similarity	NPD3949	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