NPASS Compound

Structure

NPC189068 OpenBabel07101719152D 21 23 0 0 1 0 0 0 0 0999 V2000 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7917 0.0909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 -0.6522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3305 -1.6303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4644 -2.1303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -1.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 N 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 0.7431 -1.6691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7698 -0.1170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2440 -2.0371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3599 -3.1249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1280 -0.5477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 17 1 0 0 0 0 3 13 2 0 0 0 0 3 16 1 0 0 0 0 4 2 1 6 0 0 0 4 6 1 0 0 0 0 4 21 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 18 1 1 0 0 0 7 10 1 0 0 0 0 7 19 1 1 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 16 1 6 0 0 0 10 21 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	297.11
Volume:	261.532
LogP:	-1.987
LogD:	-1.23
LogS:	-1.38
# Rotatable Bonds:	3
TPSA:	149.5
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	4.311
Fsp3:	0.545
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:	-6.12
MDCK Permeability:	2.81642351183109e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.839
Human Intestinal Absorption (HIA):	0.587
20% Bioavailability (F20%):	0.913
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.434
Plasma Protein Binding (PPB):	26.041337966918945%
Volume Distribution (VD):	1.614
Pgp-substrate:	68.98778533935547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.161
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	6.063
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.201
Rat Oral Acute Toxicity:	0.455
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.039
Carcinogencity:	0.317
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.763

Download Data

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

Natural Product: NPC189068

Natural Product ID:	NPC189068
*Common Name:**	Spongosine
IUPAC Name:	(2R,3R,4S,5R)-2-(6-amino-2-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Synonyms:	Spongosine
Standard InCHIKey:	AJACDNCVEGIBNA-KQYNXXCUSA-N
Standard InCHI:	InChI=1S/C11H15N5O5/c1-20-11-14-8(12)5-9(15-11)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7-,10-/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(OC)nc2N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470888
PubChem CID:	9796227
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0000479] Purine nucleosides

*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
NPO30675	Vibrio harveyi	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23305926]
NPO30675	Vibrio harveyi	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25668560]
NPO30675	Vibrio harveyi	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	PMID[311472]

☑ 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	2
Others	6

Activity Type	# Activity
Cell Line	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	60.0	%	PMID[523225]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	15.3	mg.kg-1	PMID[523223]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	12.5	mg.kg-1	PMID[523223]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	BP	=	-41.0	%	PMID[523223]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	HR	=	-25.0	%	PMID[523223]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	25.0	%	PMID[523223]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	56.0	%	PMID[523223]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	57.0	%	PMID[523223]

☑ 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 NPC189068 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	698
0.1-0.2	28057
0.2-0.3	9007
0.3-0.4	3935
0.4-0.5	659
0.5-0.6	145
0.6-0.7	81
0.7-0.8	39
0.8-0.85	28
0.85-0.9	12
0.9-0.95	22
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC156461
0.9925	High Similarity	NPC21448
0.9925	High Similarity	NPC219313
0.9925	High Similarity	NPC107374
0.9925	High Similarity	NPC309832
0.9851	High Similarity	NPC164665
0.9778	High Similarity	NPC269827
0.9774	High Similarity	NPC229974
0.9624	High Similarity	NPC161659
0.9624	High Similarity	NPC317821
0.9624	High Similarity	NPC209525
0.9496	High Similarity	NPC211025
0.9496	High Similarity	NPC185991
0.9496	High Similarity	NPC85689
0.9481	High Similarity	NPC314152
0.9429	High Similarity	NPC321814
0.9429	High Similarity	NPC472816
0.9362	High Similarity	NPC302778
0.9362	High Similarity	NPC130586
0.9362	High Similarity	NPC212551
0.9362	High Similarity	NPC164952
0.9301	High Similarity	NPC239737
0.9296	High Similarity	NPC174802
0.9281	High Similarity	NPC121222
0.9231	High Similarity	NPC224076
0.9167	High Similarity	NPC316618
0.9167	High Similarity	NPC226245
0.9155	High Similarity	NPC207633
0.9118	High Similarity	NPC129756
0.9085	High Similarity	NPC161224
0.9078	High Similarity	NPC136349
0.9014	High Similarity	NPC150853
0.8904	High Similarity	NPC311197
0.8904	High Similarity	NPC313754
0.8904	High Similarity	NPC54320
0.8897	High Similarity	NPC320818
0.8859	High Similarity	NPC323091
0.8836	High Similarity	NPC52238
0.8768	High Similarity	NPC33996
0.8759	High Similarity	NPC328479
0.8591	High Similarity	NPC195140
0.8497	Intermediate Similarity	NPC261595
0.8471	Intermediate Similarity	NPC189261
0.8442	Intermediate Similarity	NPC324033
0.8442	Intermediate Similarity	NPC321458
0.8408	Intermediate Similarity	NPC326529
0.84	Intermediate Similarity	NPC93365
0.8377	Intermediate Similarity	NPC325906
0.8354	Intermediate Similarity	NPC319100
0.8354	Intermediate Similarity	NPC324198
0.8312	Intermediate Similarity	NPC324484
0.8269	Intermediate Similarity	NPC326082
0.8269	Intermediate Similarity	NPC290959
0.8227	Intermediate Similarity	NPC61198
0.8156	Intermediate Similarity	NPC262926
0.8133	Intermediate Similarity	NPC321052
0.8063	Intermediate Similarity	NPC313897
0.7986	Intermediate Similarity	NPC30326
0.7958	Intermediate Similarity	NPC319221
0.7905	Intermediate Similarity	NPC89147
0.7905	Intermediate Similarity	NPC274384
0.7887	Intermediate Similarity	NPC324009
0.7838	Intermediate Similarity	NPC251233
0.7838	Intermediate Similarity	NPC211820
0.7831	Intermediate Similarity	NPC24589
0.7823	Intermediate Similarity	NPC186619
0.7798	Intermediate Similarity	NPC282458
0.7798	Intermediate Similarity	NPC78941
0.7785	Intermediate Similarity	NPC177169
0.7733	Intermediate Similarity	NPC64705
0.7733	Intermediate Similarity	NPC232408
0.7718	Intermediate Similarity	NPC318590
0.7667	Intermediate Similarity	NPC317746
0.7651	Intermediate Similarity	NPC74306
0.7651	Intermediate Similarity	NPC315642
0.7647	Intermediate Similarity	NPC326694
0.7588	Intermediate Similarity	NPC313514
0.7469	Intermediate Similarity	NPC33382
0.7423	Intermediate Similarity	NPC168702
0.7423	Intermediate Similarity	NPC125659
0.7333	Intermediate Similarity	NPC222174
0.7284	Intermediate Similarity	NPC14590
0.7278	Intermediate Similarity	NPC276373
0.7238	Intermediate Similarity	NPC5802
0.7222	Intermediate Similarity	NPC321393
0.7198	Intermediate Similarity	NPC157821
0.7163	Intermediate Similarity	NPC327579
0.709	Intermediate Similarity	NPC476564
0.7047	Intermediate Similarity	NPC57279
0.7027	Intermediate Similarity	NPC104011
0.6992	Remote Similarity	NPC87981
0.6992	Remote Similarity	NPC174114
0.6918	Remote Similarity	NPC248007
0.6913	Remote Similarity	NPC246193
0.6769	Remote Similarity	NPC250178
0.6714	Remote Similarity	NPC312187
0.6714	Remote Similarity	NPC4837
0.6712	Remote Similarity	NPC139776
0.6579	Remote Similarity	NPC287876
0.6561	Remote Similarity	NPC103388
0.6535	Remote Similarity	NPC107160
0.652	Remote Similarity	NPC160666
0.6513	Remote Similarity	NPC14330
0.6506	Remote Similarity	NPC472834
0.6475	Remote Similarity	NPC18335
0.6439	Remote Similarity	NPC21461
0.6425	Remote Similarity	NPC158055
0.64	Remote Similarity	NPC109322
0.6216	Remote Similarity	NPC68938
0.6201	Remote Similarity	NPC164845
0.6196	Remote Similarity	NPC217656
0.6159	Remote Similarity	NPC89139
0.6149	Remote Similarity	NPC296437
0.6144	Remote Similarity	NPC180493
0.6122	Remote Similarity	NPC313547
0.6118	Remote Similarity	NPC5707
0.6111	Remote Similarity	NPC470266
0.6099	Remote Similarity	NPC476561
0.6048	Remote Similarity	NPC244700
0.6037	Remote Similarity	NPC476433
0.6037	Remote Similarity	NPC476528
0.6	Remote Similarity	NPC476013
0.6	Remote Similarity	NPC476520
0.6	Remote Similarity	NPC474986
0.6	Remote Similarity	NPC189314
0.6	Remote Similarity	NPC476522
0.5988	Remote Similarity	NPC472833
0.5988	Remote Similarity	NPC476408
0.5972	Remote Similarity	NPC119133
0.5968	Remote Similarity	NPC265111
0.5964	Remote Similarity	NPC476521
0.5924	Remote Similarity	NPC473585
0.5903	Remote Similarity	NPC476099
0.5886	Remote Similarity	NPC472832
0.5886	Remote Similarity	NPC18308
0.5793	Remote Similarity	NPC476562
0.5759	Remote Similarity	NPC180462
0.5758	Remote Similarity	NPC210947
0.5734	Remote Similarity	NPC293163
0.5733	Remote Similarity	NPC256849
0.5733	Remote Similarity	NPC41958
0.5724	Remote Similarity	NPC59314
0.5724	Remote Similarity	NPC10466
0.5705	Remote Similarity	NPC47936
0.5671	Remote Similarity	NPC470140
0.5663	Remote Similarity	NPC470139
0.5658	Remote Similarity	NPC63433
0.5636	Remote Similarity	NPC470141
0.5629	Remote Similarity	NPC303899
0.561	Remote Similarity	NPC126634

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 NPC189068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	2171
0.2-0.3	3217
0.3-0.4	2207
0.4-0.5	979
0.5-0.6	169
0.6-0.7	133
0.7-0.8	67
0.8-0.85	13
0.85-0.9	10
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9925	High Similarity	NPD250	Approved
0.9925	High Similarity	NPD249	Approved
0.9778	High Similarity	NPD195	Approved
0.9778	High Similarity	NPD186	Discovery
0.95	High Similarity	NPD3107	Discontinued
0.9496	High Similarity	NPD283	Approved
0.9481	High Similarity	NPD185	Approved
0.9362	High Similarity	NPD1750	Clinical (unspecified phase)
0.9362	High Similarity	NPD1369	Phase 2
0.9362	High Similarity	NPD242	Approved
0.9362	High Similarity	NPD338	Approved
0.9343	High Similarity	NPD166	Approved
0.9333	High Similarity	NPD193	Suspended
0.9301	High Similarity	NPD2646	Discontinued
0.9301	High Similarity	NPD2624	Phase 2
0.9296	High Similarity	NPD339	Approved
0.9231	High Similarity	NPD169	Phase 2
0.9167	High Similarity	NPD1732	Phase 3
0.9078	High Similarity	NPD548	Clinical (unspecified phase)
0.8904	High Similarity	NPD217	Approved
0.8904	High Similarity	NPD220	Clinical (unspecified phase)
0.8904	High Similarity	NPD216	Approved
0.8904	High Similarity	NPD219	Phase 3
0.8904	High Similarity	NPD218	Approved
0.8699	High Similarity	NPD213	Clinical (unspecified phase)
0.8699	High Similarity	NPD214	Approved
0.8684	High Similarity	NPD2647	Phase 3
0.8529	High Similarity	NPD248	Discontinued
0.8526	High Similarity	NPD5666	Phase 2
0.8497	Intermediate Similarity	NPD247	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD7988	Suspended
0.8418	Intermediate Similarity	NPD1412	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD546	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD9632	Phase 3
0.8377	Intermediate Similarity	NPD1777	Approved
0.8377	Intermediate Similarity	NPD1776	Approved
0.8354	Intermediate Similarity	NPD4171	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD3083	Approved
0.8248	Intermediate Similarity	NPD870	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD252	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD4716	Approved
0.816	Intermediate Similarity	NPD1692	Approved
0.8148	Intermediate Similarity	NPD4744	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD549	Approved
0.8061	Intermediate Similarity	NPD6417	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5683	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5682	Phase 3
0.8061	Intermediate Similarity	NPD5684	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD516	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD2630	Approved
0.7964	Intermediate Similarity	NPD2631	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD2632	Approved
0.7929	Intermediate Similarity	NPD9633	Phase 3
0.7902	Intermediate Similarity	NPD194	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7158	Phase 1
0.7778	Intermediate Similarity	NPD536	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD9408	Phase 3
0.7651	Intermediate Similarity	NPD582	Approved
0.7647	Intermediate Similarity	NPD3708	Phase 2
0.7588	Intermediate Similarity	NPD7138	Phase 2
0.7421	Intermediate Similarity	NPD4074	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3085	Phase 1
0.7372	Intermediate Similarity	NPD3086	Phase 3
0.7348	Intermediate Similarity	NPD2965	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD231	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2877	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2876	Phase 3
0.7299	Intermediate Similarity	NPD4054	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3696	Approved
0.7285	Intermediate Similarity	NPD3695	Approved
0.7228	Intermediate Similarity	NPD2824	Phase 2
0.7215	Intermediate Similarity	NPD9605	Phase 3
0.7214	Intermediate Similarity	NPD9606	Approved
0.7176	Intermediate Similarity	NPD1046	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD9607	Approved
0.7	Intermediate Similarity	NPD209	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD171	Discontinued
0.6984	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2902	Phase 2
0.6933	Remote Similarity	NPD545	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1063	Phase 2
0.6923	Remote Similarity	NPD4240	Approved
0.6918	Remote Similarity	NPD9084	Phase 2
0.6879	Remote Similarity	NPD9374	Approved
0.6878	Remote Similarity	NPD4495	Phase 1
0.6867	Remote Similarity	NPD282	Approved
0.6857	Remote Similarity	NPD9373	Approved
0.6842	Remote Similarity	NPD1119	Phase 2
0.6835	Remote Similarity	NPD1730	Discontinued
0.6832	Remote Similarity	NPD353	Discontinued
0.6826	Remote Similarity	NPD527	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD547	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD307	Approved
0.6688	Remote Similarity	NPD2253	Discontinued
0.6688	Remote Similarity	NPD1430	Approved
0.6688	Remote Similarity	NPD1431	Approved
0.6667	Remote Similarity	NPD9083	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5080	Phase 2
0.6667	Remote Similarity	NPD1058	Discontinued
0.6646	Remote Similarity	NPD775	Approved
0.6615	Remote Similarity	NPD5079	Phase 2
0.6584	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8829	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1127	Approved
0.6556	Remote Similarity	NPD1128	Approved
0.6533	Remote Similarity	NPD281	Approved
0.6528	Remote Similarity	NPD9584	Phase 2
0.6497	Remote Similarity	NPD1808	Phase 1
0.6497	Remote Similarity	NPD799	Phase 1
0.6484	Remote Similarity	NPD207	Discontinued
0.6475	Remote Similarity	NPD8836	Approved
0.6455	Remote Similarity	NPD4458	Phase 2
0.6455	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6840	Approved
0.6419	Remote Similarity	NPD9409	Discontinued
0.6415	Remote Similarity	NPD1118	Discontinued
0.6369	Remote Similarity	NPD1121	Approved
0.6369	Remote Similarity	NPD1120	Approved
0.6369	Remote Similarity	NPD535	Approved
0.6357	Remote Similarity	NPD9626	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD9416	Phase 3
0.6338	Remote Similarity	NPD9417	Phase 3
0.6329	Remote Similarity	NPD6112	Approved
0.6319	Remote Similarity	NPD9375	Discontinued
0.6291	Remote Similarity	NPD798	Discontinued
0.6279	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD1816	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5486	Discontinued
0.6235	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD9484	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD515	Phase 1
0.6154	Remote Similarity	NPD5458	Discontinued
0.6144	Remote Similarity	NPD78	Approved
0.6144	Remote Similarity	NPD9544	Approved
0.6131	Remote Similarity	NPD7842	Phase 2
0.6129	Remote Similarity	NPD8250	Phase 2
0.6118	Remote Similarity	NPD8830	Phase 3
0.6081	Remote Similarity	NPD757	Phase 3
0.6081	Remote Similarity	NPD9406	Approved
0.6073	Remote Similarity	NPD691	Discontinued
0.6067	Remote Similarity	NPD9360	Approved
0.6	Remote Similarity	NPD1368	Approved
0.6	Remote Similarity	NPD8831	Approved
0.6	Remote Similarity	NPD8833	Approved
0.5972	Remote Similarity	NPD9291	Approved
0.5962	Remote Similarity	NPD1775	Approved
0.5962	Remote Similarity	NPD1085	Approved
0.596	Remote Similarity	NPD796	Phase 2
0.596	Remote Similarity	NPD237	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD2221	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5627	Approved
0.5928	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5768	Phase 2
0.5904	Remote Similarity	NPD9704	Approved
0.588	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD534	Phase 2
0.5874	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD537	Phase 2
0.5855	Remote Similarity	NPD578	Discontinued
0.5817	Remote Similarity	NPD6381	Phase 2
0.5817	Remote Similarity	NPD580	Discontinued
0.5816	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD1017	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD3697	Discontinued
0.5767	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.574	Remote Similarity	NPD5171	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD4089	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD9358	Approved
0.5733	Remote Similarity	NPD9359	Approved
0.5733	Remote Similarity	NPD6023	Discontinued
0.5732	Remote Similarity	NPD579	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD34	Approved
0.5729	Remote Similarity	NPD4714	Approved
0.5724	Remote Similarity	NPD8837	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD1355	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD1354	Approved
0.5723	Remote Similarity	NPD1356	Approved
0.5684	Remote Similarity	NPD5757	Discontinued
0.5684	Remote Similarity	NPD2591	Phase 2
0.5682	Remote Similarity	NPD5337	Phase 1
0.5682	Remote Similarity	NPD5336	Phase 1
0.5677	Remote Similarity	NPD9290	Approved
0.5672	Remote Similarity	NPD7323	Phase 2
0.5661	Remote Similarity	NPD2457	Phase 2
0.5661	Remote Similarity	NPD2456	Phase 2
0.566	Remote Similarity	NPD9366	Approved
0.5659	Remote Similarity	NPD9582	Phase 3
0.5638	Remote Similarity	NPD613	Phase 2
0.5636	Remote Similarity	NPD9551	Approved
0.5636	Remote Similarity	NPD9550	Approved
0.5635	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD245	Suspended
0.5616	Remote Similarity	NPD4612	Discontinued
0.5605	Remote Similarity	NPD4262	Discontinued
0.56	Remote Similarity	NPD1731	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