NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	184.04
Volume:	171.773
LogP:	1.115
LogD:	1.118
LogS:	-1.316
# Rotatable Bonds:	4
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	2.075
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.634
MDCK Permeability:	2.0847301129833795e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.846

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.228
Plasma Protein Binding (PPB):	52.94096374511719%
Volume Distribution (VD):	0.245
Pgp-substrate:	68.28410339355469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.356
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	2.193
Half-life (T1/2):	0.944

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.82
Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.151
Carcinogencity:	0.841
Eye Corrosion:	0.066
Eye Irritation:	0.945
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC272487

Natural Product ID:	NPC272487
*Common Name:**	Acetyl Sumiki's Acid
IUPAC Name:	5-(acetyloxymethyl)furan-2-carboxylic acid
Synonyms:	Acetyl Sumiki's acid
Standard InCHIKey:	VEHIMKWMEKVUMD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8O5/c1-5(9)12-4-6-2-3-7(13-6)8(10)11/h2-3H,4H2,1H3,(H,10,11)
SMILES:	CC(=O)OCc1ccc(o1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464357
PubChem CID:	10330015
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000076] Furans [CHEMONTID:0004758] Furoic acid and derivatives [CHEMONTID:0001448] Furoic acids

*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
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325242]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038560]
NPO25146	Epicoccum sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17966985]
NPO40434	Chaetomium nigricolor	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32163284]
NPO25146	Epicoccum sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	IZ	=	7.0	mm	PMID[468438]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	7.0	mm	PMID[468438]

☑ 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 NPC272487 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	295
0.1-0.2	2275
0.2-0.3	7188
0.3-0.4	10945
0.4-0.5	7052
0.5-0.6	7954
0.6-0.7	6712
0.7-0.8	261
0.8-0.85	8
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC244293
0.9474	High Similarity	NPC328451
0.906	High Similarity	NPC107482
0.8879	High Similarity	NPC311987
0.8621	High Similarity	NPC229387
0.856	High Similarity	NPC52035
0.8435	Intermediate Similarity	NPC298087
0.8376	Intermediate Similarity	NPC209111
0.8362	Intermediate Similarity	NPC219969
0.8195	Intermediate Similarity	NPC303217
0.8065	Intermediate Similarity	NPC21831
0.8065	Intermediate Similarity	NPC187547
0.8015	Intermediate Similarity	NPC107571
0.7931	Intermediate Similarity	NPC217226
0.7886	Intermediate Similarity	NPC292036
0.7857	Intermediate Similarity	NPC218712
0.7857	Intermediate Similarity	NPC307346
0.7857	Intermediate Similarity	NPC267004
0.7857	Intermediate Similarity	NPC261733
0.7845	Intermediate Similarity	NPC156768
0.7823	Intermediate Similarity	NPC11821
0.7778	Intermediate Similarity	NPC254958
0.7778	Intermediate Similarity	NPC291619
0.776	Intermediate Similarity	NPC76844
0.7752	Intermediate Similarity	NPC291189
0.7752	Intermediate Similarity	NPC69403
0.7667	Intermediate Similarity	NPC42471
0.766	Intermediate Similarity	NPC110305
0.7652	Intermediate Similarity	NPC475236
0.7652	Intermediate Similarity	NPC471501
0.7652	Intermediate Similarity	NPC471554
0.7652	Intermediate Similarity	NPC473355
0.7652	Intermediate Similarity	NPC471573
0.7634	Intermediate Similarity	NPC221798
0.7632	Intermediate Similarity	NPC233791
0.763	Intermediate Similarity	NPC104854
0.7619	Intermediate Similarity	NPC476031
0.7619	Intermediate Similarity	NPC476014
0.7597	Intermediate Similarity	NPC474136
0.7581	Intermediate Similarity	NPC26157
0.7581	Intermediate Similarity	NPC1811
0.7571	Intermediate Similarity	NPC282973
0.7571	Intermediate Similarity	NPC148374
0.7551	Intermediate Similarity	NPC474378
0.7551	Intermediate Similarity	NPC474219
0.7538	Intermediate Similarity	NPC283284
0.7538	Intermediate Similarity	NPC289911
0.7535	Intermediate Similarity	NPC254198
0.7519	Intermediate Similarity	NPC474817
0.7519	Intermediate Similarity	NPC474830
0.7518	Intermediate Similarity	NPC288209
0.75	Intermediate Similarity	NPC474829
0.75	Intermediate Similarity	NPC471559
0.75	Intermediate Similarity	NPC146316
0.75	Intermediate Similarity	NPC97740
0.75	Intermediate Similarity	NPC45358
0.7481	Intermediate Similarity	NPC475818
0.7481	Intermediate Similarity	NPC476351
0.748	Intermediate Similarity	NPC474987
0.7466	Intermediate Similarity	NPC2063
0.7464	Intermediate Similarity	NPC14650
0.7458	Intermediate Similarity	NPC132725
0.7442	Intermediate Similarity	NPC61779
0.7438	Intermediate Similarity	NPC17537
0.7432	Intermediate Similarity	NPC471613
0.7426	Intermediate Similarity	NPC17681
0.7413	Intermediate Similarity	NPC22248
0.7405	Intermediate Similarity	NPC174915
0.7405	Intermediate Similarity	NPC270807
0.7379	Intermediate Similarity	NPC104924
0.7368	Intermediate Similarity	NPC75557
0.7368	Intermediate Similarity	NPC71274
0.7365	Intermediate Similarity	NPC116822
0.7357	Intermediate Similarity	NPC170604
0.7357	Intermediate Similarity	NPC215109
0.7347	Intermediate Similarity	NPC280025
0.7333	Intermediate Similarity	NPC474438
0.7333	Intermediate Similarity	NPC474279
0.7313	Intermediate Similarity	NPC474260
0.7313	Intermediate Similarity	NPC81912
0.7313	Intermediate Similarity	NPC329694
0.7313	Intermediate Similarity	NPC329922
0.731	Intermediate Similarity	NPC37488
0.731	Intermediate Similarity	NPC195920
0.7303	Intermediate Similarity	NPC104380
0.7303	Intermediate Similarity	NPC473282
0.7303	Intermediate Similarity	NPC217602
0.7297	Intermediate Similarity	NPC228842
0.7293	Intermediate Similarity	NPC118853
0.729	Intermediate Similarity	NPC475779
0.7279	Intermediate Similarity	NPC2596
0.726	Intermediate Similarity	NPC475864
0.7259	Intermediate Similarity	NPC137570
0.7258	Intermediate Similarity	NPC473356
0.7258	Intermediate Similarity	NPC471521
0.7241	Intermediate Similarity	NPC137295
0.7234	Intermediate Similarity	NPC64230
0.7234	Intermediate Similarity	NPC71638
0.7234	Intermediate Similarity	NPC473268
0.7234	Intermediate Similarity	NPC294470
0.7231	Intermediate Similarity	NPC94298
0.7231	Intermediate Similarity	NPC27633
0.7222	Intermediate Similarity	NPC184053
0.7211	Intermediate Similarity	NPC474317
0.72	Intermediate Similarity	NPC121615
0.72	Intermediate Similarity	NPC177331
0.72	Intermediate Similarity	NPC294511
0.719	Intermediate Similarity	NPC476930
0.719	Intermediate Similarity	NPC294300
0.719	Intermediate Similarity	NPC317900
0.719	Intermediate Similarity	NPC476404
0.7176	Intermediate Similarity	NPC4898
0.7174	Intermediate Similarity	NPC285776
0.7163	Intermediate Similarity	NPC139519
0.7162	Intermediate Similarity	NPC474220
0.7162	Intermediate Similarity	NPC474255
0.7162	Intermediate Similarity	NPC471618
0.7154	Intermediate Similarity	NPC217180
0.7154	Intermediate Similarity	NPC312525
0.7154	Intermediate Similarity	NPC131801
0.7153	Intermediate Similarity	NPC326065
0.7153	Intermediate Similarity	NPC2401
0.7153	Intermediate Similarity	NPC248795
0.7143	Intermediate Similarity	NPC159418
0.7143	Intermediate Similarity	NPC287559
0.7143	Intermediate Similarity	NPC291153
0.7143	Intermediate Similarity	NPC283823
0.7132	Intermediate Similarity	NPC205523
0.7132	Intermediate Similarity	NPC220540
0.7132	Intermediate Similarity	NPC476016
0.7123	Intermediate Similarity	NPC476164
0.7123	Intermediate Similarity	NPC473090
0.7123	Intermediate Similarity	NPC476310
0.7122	Intermediate Similarity	NPC471544
0.7122	Intermediate Similarity	NPC473344
0.7122	Intermediate Similarity	NPC471545
0.7115	Intermediate Similarity	NPC261184
0.7114	Intermediate Similarity	NPC475904
0.7114	Intermediate Similarity	NPC474270
0.7105	Intermediate Similarity	NPC84721
0.7097	Intermediate Similarity	NPC18986
0.7092	Intermediate Similarity	NPC159786
0.7083	Intermediate Similarity	NPC475045
0.7083	Intermediate Similarity	NPC473988
0.7078	Intermediate Similarity	NPC473368
0.7077	Intermediate Similarity	NPC131192
0.7077	Intermediate Similarity	NPC470860
0.7075	Intermediate Similarity	NPC213900
0.7075	Intermediate Similarity	NPC10302
0.7075	Intermediate Similarity	NPC105381
0.7071	Intermediate Similarity	NPC474407
0.7071	Intermediate Similarity	NPC111888
0.7071	Intermediate Similarity	NPC474425
0.7071	Intermediate Similarity	NPC474426
0.7067	Intermediate Similarity	NPC226578
0.7067	Intermediate Similarity	NPC477941
0.7059	Intermediate Similarity	NPC268008
0.7059	Intermediate Similarity	NPC80489
0.7059	Intermediate Similarity	NPC469485
0.7055	Intermediate Similarity	NPC150023
0.7055	Intermediate Similarity	NPC27220
0.7055	Intermediate Similarity	NPC242756
0.705	Intermediate Similarity	NPC109778
0.7047	Intermediate Similarity	NPC129650
0.7045	Intermediate Similarity	NPC473969
0.7045	Intermediate Similarity	NPC244862
0.7045	Intermediate Similarity	NPC67345
0.7042	Intermediate Similarity	NPC212729
0.7039	Intermediate Similarity	NPC60211
0.7034	Intermediate Similarity	NPC79908
0.7034	Intermediate Similarity	NPC230902
0.7034	Intermediate Similarity	NPC80098
0.7032	Intermediate Similarity	NPC228501
0.7027	Intermediate Similarity	NPC316535
0.7023	Intermediate Similarity	NPC144745
0.7023	Intermediate Similarity	NPC227660
0.7023	Intermediate Similarity	NPC208906
0.7021	Intermediate Similarity	NPC66158
0.7021	Intermediate Similarity	NPC106247
0.7015	Intermediate Similarity	NPC473379
0.7015	Intermediate Similarity	NPC471549
0.7014	Intermediate Similarity	NPC474943
0.7014	Intermediate Similarity	NPC284409
0.7014	Intermediate Similarity	NPC474615
0.7014	Intermediate Similarity	NPC475005
0.7014	Intermediate Similarity	NPC325625
0.7014	Intermediate Similarity	NPC254841
0.7014	Intermediate Similarity	NPC287068
0.7013	Intermediate Similarity	NPC88007
0.7013	Intermediate Similarity	NPC173544
0.7013	Intermediate Similarity	NPC19860
0.7013	Intermediate Similarity	NPC194499
0.7013	Intermediate Similarity	NPC7059
0.7007	Intermediate Similarity	NPC184391
0.7006	Intermediate Similarity	NPC219861
0.7	Intermediate Similarity	NPC471817
0.7	Intermediate Similarity	NPC473982
0.7	Intermediate Similarity	NPC211811
0.6993	Remote Similarity	NPC301233
0.6993	Remote Similarity	NPC163029

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 NPC272487 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	1167
0.2-0.3	2502
0.3-0.4	2813
0.4-0.5	1574
0.5-0.6	658
0.6-0.7	182
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.906	High Similarity	NPD9092	Discovery
0.7444	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD9545	Approved
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.702	Intermediate Similarity	NPD6599	Discontinued
0.6993	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7075	Discontinued
0.6963	Remote Similarity	NPD9717	Approved
0.6939	Remote Similarity	NPD2354	Approved
0.6933	Remote Similarity	NPD5403	Approved
0.6928	Remote Similarity	NPD6801	Discontinued
0.6913	Remote Similarity	NPD5401	Approved
0.6903	Remote Similarity	NPD3882	Suspended
0.6884	Remote Similarity	NPD5647	Approved
0.6815	Remote Similarity	NPD919	Approved
0.6794	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1471	Phase 3
0.6753	Remote Similarity	NPD7411	Suspended
0.6731	Remote Similarity	NPD3817	Phase 2
0.6728	Remote Similarity	NPD2163	Approved
0.6723	Remote Similarity	NPD9365	Approved
0.6715	Remote Similarity	NPD1608	Approved
0.6714	Remote Similarity	NPD9494	Approved
0.6712	Remote Similarity	NPD1551	Phase 2
0.6711	Remote Similarity	NPD3887	Approved
0.6691	Remote Similarity	NPD1203	Approved
0.669	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6765	Approved
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD2353	Approved
0.6645	Remote Similarity	NPD958	Approved
0.6643	Remote Similarity	NPD6233	Phase 2
0.6643	Remote Similarity	NPD4062	Phase 3
0.6641	Remote Similarity	NPD1358	Approved
0.6641	Remote Similarity	NPD769	Approved
0.664	Remote Similarity	NPD291	Approved
0.6625	Remote Similarity	NPD1247	Approved
0.6624	Remote Similarity	NPD5402	Approved
0.6622	Remote Similarity	NPD1549	Phase 2
0.6619	Remote Similarity	NPD3225	Approved
0.6618	Remote Similarity	NPD1778	Approved
0.6601	Remote Similarity	NPD920	Approved
0.6591	Remote Similarity	NPD1241	Discontinued
0.6577	Remote Similarity	NPD1243	Approved
0.6573	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3268	Approved
0.6556	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2344	Approved
0.6552	Remote Similarity	NPD4340	Discontinued
0.6531	Remote Similarity	NPD7033	Discontinued
0.6525	Remote Similarity	NPD1019	Discontinued
0.6516	Remote Similarity	NPD3226	Approved
0.6513	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6785	Approved
0.6509	Remote Similarity	NPD6784	Approved
0.6503	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD17	Approved
0.6483	Remote Similarity	NPD1240	Approved
0.6471	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD411	Approved
0.6452	Remote Similarity	NPD957	Approved
0.6444	Remote Similarity	NPD9493	Approved
0.6438	Remote Similarity	NPD3749	Approved
0.6434	Remote Similarity	NPD6832	Phase 2
0.6429	Remote Similarity	NPD1512	Approved
0.6429	Remote Similarity	NPD5049	Phase 3
0.6424	Remote Similarity	NPD3750	Approved
0.6424	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD1510	Phase 2
0.64	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1607	Approved
0.6392	Remote Similarity	NPD1934	Approved
0.6385	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2309	Approved
0.6375	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD7819	Suspended
0.6345	Remote Similarity	NPD2313	Discontinued
0.6345	Remote Similarity	NPD3764	Approved
0.6338	Remote Similarity	NPD3267	Approved
0.6338	Remote Similarity	NPD3266	Approved
0.6335	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD1933	Approved
0.6316	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD4308	Phase 3
0.6309	Remote Similarity	NPD2799	Discontinued
0.6308	Remote Similarity	NPD3134	Approved
0.6303	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD1511	Approved
0.629	Remote Similarity	NPD9296	Approved
0.6288	Remote Similarity	NPD556	Approved
0.6287	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD1212	Approved
0.6286	Remote Similarity	NPD422	Phase 1
0.6286	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6653	Approved
0.6282	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD7095	Approved
0.6275	Remote Similarity	NPD6190	Approved
0.6272	Remote Similarity	NPD6559	Discontinued
0.6267	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD2796	Approved
0.6266	Remote Similarity	NPD4380	Phase 2
0.626	Remote Similarity	NPD290	Approved
0.6259	Remote Similarity	NPD4060	Phase 1
0.6258	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD3146	Approved
0.625	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2801	Approved
0.625	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD1481	Phase 2
0.6235	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD1048	Approved
0.6232	Remote Similarity	NPD1894	Discontinued
0.6228	Remote Similarity	NPD3818	Discontinued
0.6228	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD5762	Approved
0.6225	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD6005	Phase 3
0.6225	Remote Similarity	NPD6004	Phase 3
0.6225	Remote Similarity	NPD6002	Phase 3
0.6225	Remote Similarity	NPD5763	Approved
0.6225	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD987	Approved
0.6224	Remote Similarity	NPD6362	Approved
0.6224	Remote Similarity	NPD2797	Approved
0.6222	Remote Similarity	NPD9069	Phase 1
0.6218	Remote Similarity	NPD2186	Approved
0.6216	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD3496	Discontinued
0.6213	Remote Similarity	NPD6797	Phase 2
0.6213	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD6166	Phase 2
0.6205	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD7458	Discontinued
0.62	Remote Similarity	NPD3748	Approved
0.6197	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5958	Discontinued
0.6184	Remote Similarity	NPD4534	Discontinued
0.6176	Remote Similarity	NPD7251	Discontinued
0.617	Remote Similarity	NPD1091	Approved
0.617	Remote Similarity	NPD1535	Discovery
0.6154	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2532	Approved
0.6154	Remote Similarity	NPD2534	Approved
0.6154	Remote Similarity	NPD2533	Approved
0.6154	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD9501	Approved
0.6149	Remote Similarity	NPD3142	Approved
0.6149	Remote Similarity	NPD3140	Approved
0.6148	Remote Similarity	NPD9295	Approved
0.6145	Remote Similarity	NPD3926	Phase 2
0.6145	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7808	Phase 3
0.6136	Remote Similarity	NPD9552	Approved
0.6129	Remote Similarity	NPD7440	Discontinued
0.6127	Remote Similarity	NPD3972	Approved
0.6118	Remote Similarity	NPD2346	Discontinued
0.6107	Remote Similarity	NPD9697	Approved
0.6095	Remote Similarity	NPD5844	Phase 1
0.609	Remote Similarity	NPD2684	Approved
0.6084	Remote Similarity	NPD6808	Phase 2
0.6074	Remote Similarity	NPD7768	Phase 2
0.6074	Remote Similarity	NPD969	Suspended
0.6053	Remote Similarity	NPD2935	Discontinued
0.6053	Remote Similarity	NPD5712	Approved
0.6049	Remote Similarity	NPD1465	Phase 2
0.6045	Remote Similarity	NPD2067	Discontinued
0.604	Remote Similarity	NPD4307	Phase 2
0.6039	Remote Similarity	NPD1652	Phase 2
0.6039	Remote Similarity	NPD2800	Approved
0.6036	Remote Similarity	NPD3751	Discontinued
0.6034	Remote Similarity	NPD1163	Approved
0.6034	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD7843	Approved
0.6027	Remote Similarity	NPD454	Approved
0.6026	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD6386	Approved
0.6025	Remote Similarity	NPD6385	Approved
0.6013	Remote Similarity	NPD6273	Approved
0.6012	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD4466	Phase 1
0.6	Remote Similarity	NPD7054	Approved
0.6	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6398	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