NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	269.07
Volume:	261.473
LogP:	1.22
LogD:	1.171
LogS:	-3.094
# Rotatable Bonds:	0
TPSA:	68.54
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	4.035
Fsp3:	0.2
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:	-4.789
MDCK Permeability:	2.1516885681194253e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.191
Plasma Protein Binding (PPB):	82.5794448852539%
Volume Distribution (VD):	0.787
Pgp-substrate:	15.141074180603027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.744
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.567
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.364
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.831
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	4.632
Half-life (T1/2):	0.357

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.631
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.117
Rat Oral Acute Toxicity:	0.852
Maximum Recommended Daily Dose:	0.708
Skin Sensitization:	0.473
Carcinogencity:	0.888
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.479

Download Data

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

Natural Product: NPC105541

Natural Product ID:	NPC105541
*Common Name:**	(2S)-Spiro[Pyrano[3,2-C]Chromene-2,4'-Pyrrolidine]-2',5-Dione
IUPAC Name:	(2S)-spiro[pyrano[3,2-c]chromene-2,4'-pyrrolidine]-2',5-dione
Synonyms:
Standard InCHIKey:	WDXSHNYCSJAKJI-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C15H11NO4/c17-12-7-15(8-16-12)6-5-10-13(20-15)9-3-1-2-4-11(9)19-14(10)18/h1-6H,7-8H2,(H,16,17)/t15-/m1/s1
SMILES:	OC1=NC[C@]2(C1)C=Cc1c(O2)c2ccccc2oc1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1956008
PubChem CID:	57402648
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO33397	tetramorium sp.	Species	Formicidae	Eukaryota	n.a.	ChangBai Mountain, China	n.a.	PMID[22364815]

☑ 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	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	5.0	mm	PMID[511902]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[511902]

☑ 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 NPC105541 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	255
0.1-0.2	1716
0.2-0.3	5590
0.3-0.4	11791
0.4-0.5	5467
0.5-0.6	9590
0.6-0.7	6789
0.7-0.8	1488
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8016	Intermediate Similarity	NPC141068
0.7923	Intermediate Similarity	NPC33717
0.782	Intermediate Similarity	NPC193193
0.782	Intermediate Similarity	NPC31314
0.7795	Intermediate Similarity	NPC149545
0.7794	Intermediate Similarity	NPC229113
0.7687	Intermediate Similarity	NPC474874
0.7619	Intermediate Similarity	NPC139891
0.7538	Intermediate Similarity	NPC227553
0.7537	Intermediate Similarity	NPC5932
0.7535	Intermediate Similarity	NPC470392
0.75	Intermediate Similarity	NPC302107
0.7482	Intermediate Similarity	NPC168259
0.7481	Intermediate Similarity	NPC266116
0.7445	Intermediate Similarity	NPC52247
0.7445	Intermediate Similarity	NPC187868
0.7426	Intermediate Similarity	NPC247553
0.7407	Intermediate Similarity	NPC152306
0.7397	Intermediate Similarity	NPC471283
0.7394	Intermediate Similarity	NPC238309
0.7391	Intermediate Similarity	NPC257188
0.7391	Intermediate Similarity	NPC13007
0.7391	Intermediate Similarity	NPC311219
0.7388	Intermediate Similarity	NPC128633
0.7388	Intermediate Similarity	NPC163398
0.7353	Intermediate Similarity	NPC298796
0.7343	Intermediate Similarity	NPC2989
0.7338	Intermediate Similarity	NPC248786
0.7338	Intermediate Similarity	NPC290605
0.7338	Intermediate Similarity	NPC154176
0.7338	Intermediate Similarity	NPC173350
0.7324	Intermediate Similarity	NPC185066
0.7299	Intermediate Similarity	NPC14177
0.7279	Intermediate Similarity	NPC265547
0.7279	Intermediate Similarity	NPC317045
0.7279	Intermediate Similarity	NPC246177
0.7279	Intermediate Similarity	NPC96705
0.7273	Intermediate Similarity	NPC474289
0.7254	Intermediate Similarity	NPC258567
0.7254	Intermediate Similarity	NPC121740
0.7254	Intermediate Similarity	NPC224774
0.7246	Intermediate Similarity	NPC163200
0.7246	Intermediate Similarity	NPC319378
0.7241	Intermediate Similarity	NPC307289
0.7241	Intermediate Similarity	NPC281558
0.7239	Intermediate Similarity	NPC87563
0.7234	Intermediate Similarity	NPC244495
0.7234	Intermediate Similarity	NPC93219
0.7234	Intermediate Similarity	NPC88403
0.7226	Intermediate Similarity	NPC281356
0.7222	Intermediate Similarity	NPC113098
0.7222	Intermediate Similarity	NPC32463
0.7214	Intermediate Similarity	NPC315807
0.7209	Intermediate Similarity	NPC227255
0.7206	Intermediate Similarity	NPC263754
0.7206	Intermediate Similarity	NPC183154
0.7203	Intermediate Similarity	NPC157212
0.7203	Intermediate Similarity	NPC469453
0.7185	Intermediate Similarity	NPC296526
0.7181	Intermediate Similarity	NPC73078
0.7181	Intermediate Similarity	NPC319870
0.7181	Intermediate Similarity	NPC327612
0.7181	Intermediate Similarity	NPC148738
0.7174	Intermediate Similarity	NPC230951
0.7172	Intermediate Similarity	NPC29734
0.7172	Intermediate Similarity	NPC267336
0.7172	Intermediate Similarity	NPC471953
0.7172	Intermediate Similarity	NPC272650
0.7171	Intermediate Similarity	NPC313414
0.7163	Intermediate Similarity	NPC111347
0.7163	Intermediate Similarity	NPC291899
0.7143	Intermediate Similarity	NPC98179
0.7143	Intermediate Similarity	NPC302211
0.7143	Intermediate Similarity	NPC233238
0.7143	Intermediate Similarity	NPC131950
0.7143	Intermediate Similarity	NPC253574
0.7133	Intermediate Similarity	NPC71903
0.7133	Intermediate Similarity	NPC243688
0.7133	Intermediate Similarity	NPC142087
0.7133	Intermediate Similarity	NPC95034
0.7132	Intermediate Similarity	NPC109637
0.7123	Intermediate Similarity	NPC317601
0.7123	Intermediate Similarity	NPC169766
0.7123	Intermediate Similarity	NPC329427
0.7122	Intermediate Similarity	NPC180006
0.7122	Intermediate Similarity	NPC235190
0.7122	Intermediate Similarity	NPC307253
0.7113	Intermediate Similarity	NPC232692
0.7113	Intermediate Similarity	NPC202594
0.7101	Intermediate Similarity	NPC264976
0.7095	Intermediate Similarity	NPC281169
0.7095	Intermediate Similarity	NPC33986
0.7095	Intermediate Similarity	NPC161856
0.7095	Intermediate Similarity	NPC291119
0.7095	Intermediate Similarity	NPC51087
0.7092	Intermediate Similarity	NPC50720
0.7092	Intermediate Similarity	NPC109675
0.7092	Intermediate Similarity	NPC273772
0.7092	Intermediate Similarity	NPC472518
0.7086	Intermediate Similarity	NPC170812
0.7075	Intermediate Similarity	NPC163557
0.7075	Intermediate Similarity	NPC282477
0.7075	Intermediate Similarity	NPC284855
0.7075	Intermediate Similarity	NPC469449
0.7071	Intermediate Similarity	NPC144418
0.7063	Intermediate Similarity	NPC471826
0.7059	Intermediate Similarity	NPC51345
0.7055	Intermediate Similarity	NPC274732
0.705	Intermediate Similarity	NPC263835
0.705	Intermediate Similarity	NPC289330
0.705	Intermediate Similarity	NPC53596
0.705	Intermediate Similarity	NPC471308
0.705	Intermediate Similarity	NPC17388
0.705	Intermediate Similarity	NPC160120
0.7047	Intermediate Similarity	NPC78746
0.7047	Intermediate Similarity	NPC115861
0.7047	Intermediate Similarity	NPC188380
0.7047	Intermediate Similarity	NPC224543
0.7042	Intermediate Similarity	NPC193805
0.7042	Intermediate Similarity	NPC27671
0.7042	Intermediate Similarity	NPC89630
0.7042	Intermediate Similarity	NPC201667
0.7042	Intermediate Similarity	NPC73413
0.7031	Intermediate Similarity	NPC107101
0.7027	Intermediate Similarity	NPC62366
0.7025	Intermediate Similarity	NPC56635
0.7021	Intermediate Similarity	NPC96286
0.7021	Intermediate Similarity	NPC471314
0.7021	Intermediate Similarity	NPC248429
0.7021	Intermediate Similarity	NPC471315
0.7021	Intermediate Similarity	NPC150214
0.702	Intermediate Similarity	NPC312881
0.7015	Intermediate Similarity	NPC163674
0.7007	Intermediate Similarity	NPC194277
0.7006	Intermediate Similarity	NPC123011
0.7006	Intermediate Similarity	NPC256689
0.7	Intermediate Similarity	NPC294456
0.7	Intermediate Similarity	NPC281014
0.7	Intermediate Similarity	NPC153818
0.7	Intermediate Similarity	NPC232246
0.7	Intermediate Similarity	NPC471068
0.7	Intermediate Similarity	NPC184861
0.7	Intermediate Similarity	NPC155963
0.7	Intermediate Similarity	NPC471069
0.7	Intermediate Similarity	NPC212124
0.7	Intermediate Similarity	NPC225106
0.7	Intermediate Similarity	NPC283546
0.6993	Remote Similarity	NPC4164
0.6992	Remote Similarity	NPC79543
0.6978	Remote Similarity	NPC98748
0.6978	Remote Similarity	NPC43275
0.6978	Remote Similarity	NPC256369
0.6977	Remote Similarity	NPC307425
0.6974	Remote Similarity	NPC195357
0.6974	Remote Similarity	NPC476442
0.6974	Remote Similarity	NPC287286
0.6974	Remote Similarity	NPC152771
0.6974	Remote Similarity	NPC215512
0.6972	Remote Similarity	NPC143725
0.6966	Remote Similarity	NPC219923
0.6966	Remote Similarity	NPC2401
0.6966	Remote Similarity	NPC472519
0.6959	Remote Similarity	NPC7526
0.6959	Remote Similarity	NPC83535
0.6959	Remote Similarity	NPC1220
0.6959	Remote Similarity	NPC222036
0.6959	Remote Similarity	NPC142563
0.6959	Remote Similarity	NPC287533
0.6959	Remote Similarity	NPC241165
0.6959	Remote Similarity	NPC141822
0.6959	Remote Similarity	NPC2363
0.6959	Remote Similarity	NPC31849
0.6959	Remote Similarity	NPC205797
0.6959	Remote Similarity	NPC291551
0.6957	Remote Similarity	NPC45104
0.6954	Remote Similarity	NPC278600
0.6954	Remote Similarity	NPC47040
0.6954	Remote Similarity	NPC37428
0.6954	Remote Similarity	NPC151946
0.6954	Remote Similarity	NPC471070
0.6954	Remote Similarity	NPC212850
0.6954	Remote Similarity	NPC221046
0.6954	Remote Similarity	NPC471071
0.6954	Remote Similarity	NPC35501
0.6954	Remote Similarity	NPC279573
0.6954	Remote Similarity	NPC189724
0.6954	Remote Similarity	NPC471072
0.6954	Remote Similarity	NPC83289
0.6954	Remote Similarity	NPC144512
0.6954	Remote Similarity	NPC211110
0.6954	Remote Similarity	NPC137262
0.695	Remote Similarity	NPC476165
0.6947	Remote Similarity	NPC128730
0.6947	Remote Similarity	NPC127676
0.6944	Remote Similarity	NPC329272
0.6944	Remote Similarity	NPC188327
0.6944	Remote Similarity	NPC234109
0.6939	Remote Similarity	NPC73738
0.6939	Remote Similarity	NPC250727
0.6939	Remote Similarity	NPC37009

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 NPC105541 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	712
0.2-0.3	1222
0.3-0.4	2244
0.4-0.5	2580
0.5-0.6	1699
0.6-0.7	435
0.7-0.8	63
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7971	Intermediate Similarity	NPD1048	Approved
0.7794	Intermediate Similarity	NPD3225	Approved
0.7619	Intermediate Similarity	NPD9697	Approved
0.7483	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2797	Approved
0.7445	Intermediate Similarity	NPD422	Phase 1
0.7391	Intermediate Similarity	NPD9717	Approved
0.7357	Intermediate Similarity	NPD1203	Approved
0.7343	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD1758	Phase 1
0.7279	Intermediate Similarity	NPD1759	Phase 1
0.7254	Intermediate Similarity	NPD1712	Approved
0.7234	Intermediate Similarity	NPD3267	Approved
0.7234	Intermediate Similarity	NPD3266	Approved
0.7203	Intermediate Similarity	NPD2614	Approved
0.7179	Intermediate Similarity	NPD6502	Phase 2
0.7172	Intermediate Similarity	NPD7477	Discontinued
0.7162	Intermediate Similarity	NPD4308	Phase 3
0.7134	Intermediate Similarity	NPD2366	Approved
0.7114	Intermediate Similarity	NPD6032	Approved
0.7092	Intermediate Similarity	NPD3685	Discontinued
0.709	Intermediate Similarity	NPD821	Approved
0.7075	Intermediate Similarity	NPD654	Phase 3
0.7071	Intermediate Similarity	NPD776	Approved
0.7055	Intermediate Similarity	NPD840	Approved
0.7055	Intermediate Similarity	NPD839	Approved
0.7047	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6971	Discontinued
0.7007	Intermediate Similarity	NPD4307	Phase 2
0.7006	Intermediate Similarity	NPD5811	Approved
0.6986	Remote Similarity	NPD1296	Phase 2
0.698	Remote Similarity	NPD696	Discontinued
0.6972	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5535	Approved
0.6962	Remote Similarity	NPD6585	Discontinued
0.6959	Remote Similarity	NPD5124	Phase 1
0.6959	Remote Similarity	NPD4622	Approved
0.6959	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4618	Approved
0.6954	Remote Similarity	NPD3656	Approved
0.6951	Remote Similarity	NPD7608	Discontinued
0.6944	Remote Similarity	NPD1019	Discontinued
0.6939	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2557	Approved
0.6923	Remote Similarity	NPD6390	Discontinued
0.6918	Remote Similarity	NPD5163	Phase 2
0.6918	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2157	Approved
0.6908	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3111	Phase 1
0.6899	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4993	Discontinued
0.6897	Remote Similarity	NPD2237	Approved
0.6892	Remote Similarity	NPD2203	Discontinued
0.6887	Remote Similarity	NPD2161	Phase 2
0.6879	Remote Similarity	NPD3496	Discontinued
0.6871	Remote Similarity	NPD2313	Discontinued
0.6871	Remote Similarity	NPD411	Approved
0.6867	Remote Similarity	NPD5688	Approved
0.6867	Remote Similarity	NPD5689	Approved
0.6867	Remote Similarity	NPD1536	Approved
0.6863	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6583	Phase 3
0.6853	Remote Similarity	NPD6582	Phase 2
0.6849	Remote Similarity	NPD682	Discontinued
0.6849	Remote Similarity	NPD6832	Phase 2
0.6846	Remote Similarity	NPD447	Suspended
0.6842	Remote Similarity	NPD1375	Discontinued
0.6842	Remote Similarity	NPD290	Approved
0.6842	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7972	Discontinued
0.6824	Remote Similarity	NPD520	Approved
0.6824	Remote Similarity	NPD5745	Approved
0.6821	Remote Similarity	NPD7033	Discontinued
0.6815	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5889	Approved
0.6813	Remote Similarity	NPD5890	Approved
0.6813	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD709	Approved
0.6809	Remote Similarity	NPD1778	Approved
0.6806	Remote Similarity	NPD196	Phase 1
0.6797	Remote Similarity	NPD2424	Discontinued
0.6795	Remote Similarity	NPD4357	Discontinued
0.6795	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7318	Phase 3
0.6786	Remote Similarity	NPD2486	Discontinued
0.6786	Remote Similarity	NPD1548	Phase 1
0.6786	Remote Similarity	NPD3909	Discontinued
0.6776	Remote Similarity	NPD4477	Approved
0.6776	Remote Similarity	NPD4476	Approved
0.6776	Remote Similarity	NPD1538	Phase 1
0.6776	Remote Similarity	NPD1537	Approved
0.6776	Remote Similarity	NPD1519	Approved
0.6774	Remote Similarity	NPD3692	Discontinued
0.6761	Remote Similarity	NPD3847	Discontinued
0.6757	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1520	Approved
0.6755	Remote Similarity	NPD1521	Approved
0.6753	Remote Similarity	NPD1652	Phase 2
0.6738	Remote Similarity	NPD3049	Approved
0.6733	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1035	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6666	Approved
0.6731	Remote Similarity	NPD6667	Approved
0.673	Remote Similarity	NPD4003	Phase 3
0.6727	Remote Similarity	NPD6746	Phase 2
0.6716	Remote Similarity	NPD1358	Approved
0.6713	Remote Similarity	NPD1535	Discovery
0.6712	Remote Similarity	NPD558	Phase 2
0.6712	Remote Similarity	NPD6584	Phase 3
0.6711	Remote Similarity	NPD4108	Discontinued
0.671	Remote Similarity	NPD6331	Phase 2
0.671	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.671	Remote Similarity	NPD3750	Approved
0.6706	Remote Similarity	NPD5557	Phase 1
0.6689	Remote Similarity	NPD1024	Discontinued
0.6689	Remote Similarity	NPD5746	Approved
0.6688	Remote Similarity	NPD7153	Discontinued
0.6688	Remote Similarity	NPD7213	Phase 3
0.6688	Remote Similarity	NPD2897	Discontinued
0.6688	Remote Similarity	NPD7212	Phase 2
0.6687	Remote Similarity	NPD2415	Discontinued
0.6667	Remote Similarity	NPD7317	Phase 3
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD6581	Approved
0.6667	Remote Similarity	NPD6580	Approved
0.6667	Remote Similarity	NPD1523	Approved
0.6667	Remote Similarity	NPD592	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD468	Phase 1
0.6667	Remote Similarity	NPD1481	Phase 2
0.6667	Remote Similarity	NPD594	Approved
0.6667	Remote Similarity	NPD1522	Approved
0.6646	Remote Similarity	NPD7447	Phase 1
0.6646	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2200	Suspended
0.6644	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6798	Discontinued
0.6644	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3294	Phase 2
0.6643	Remote Similarity	NPD3596	Phase 2
0.6643	Remote Similarity	NPD9493	Approved
0.6642	Remote Similarity	NPD968	Approved
0.6642	Remote Similarity	NPD3134	Approved
0.6627	Remote Similarity	NPD5605	Phase 2
0.6626	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD9694	Discovery
0.6623	Remote Similarity	NPD1933	Approved
0.6623	Remote Similarity	NPD7030	Discontinued
0.6621	Remote Similarity	NPD1669	Approved
0.662	Remote Similarity	NPD6382	Discontinued
0.662	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6072	Discontinued
0.6605	Remote Similarity	NPD3274	Phase 2
0.6605	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3748	Approved
0.66	Remote Similarity	NPD1423	Approved
0.6597	Remote Similarity	NPD1091	Approved
0.6597	Remote Similarity	NPD1611	Approved
0.6581	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2653	Approved
0.6577	Remote Similarity	NPD3136	Phase 2
0.6577	Remote Similarity	NPD7095	Approved
0.6575	Remote Similarity	NPD2922	Phase 1
0.6573	Remote Similarity	NPD2556	Approved
0.6573	Remote Similarity	NPD2668	Approved
0.6573	Remote Similarity	NPD2554	Approved
0.6573	Remote Similarity	NPD2667	Approved
0.6573	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6671	Approved
0.6562	Remote Similarity	NPD7131	Phase 3
0.6562	Remote Similarity	NPD7427	Discontinued
0.6558	Remote Similarity	NPD2239	Approved
0.6558	Remote Similarity	NPD1725	Approved
0.6558	Remote Similarity	NPD2240	Approved
0.6556	Remote Similarity	NPD1393	Approved
0.6556	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2235	Phase 2
0.6552	Remote Similarity	NPD2230	Approved
0.6552	Remote Similarity	NPD2231	Phase 2
0.6552	Remote Similarity	NPD2233	Approved
0.6552	Remote Similarity	NPD2232	Approved
0.6552	Remote Similarity	NPD1608	Approved
0.6548	Remote Similarity	NPD7315	Approved
0.6547	Remote Similarity	NPD1241	Discontinued
0.6541	Remote Similarity	NPD3985	Discontinued
0.6541	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2505	Approved
0.6541	Remote Similarity	NPD7019	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