NPASS Compound

Structure

NPC228318 OpenBabel07101719512D 21 24 0 0 0 0 0 0 0 0999 V2000 4.3301 0.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.4140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4763 -0.2890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4763 -0.2890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 14 2 0 0 0 0 9 10 2 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 13 1 0 0 0 0 12 15 2 0 0 0 0 13 16 2 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 16 18 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	274.06
Volume:	285.664
LogP:	4.094
LogD:	3.427
LogS:	-4.798
# Rotatable Bonds:	1
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	2.118
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.781
MDCK Permeability:	2.439961644995492e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.118
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	98.25050354003906%
Volume Distribution (VD):	0.582
Pgp-substrate:	1.3622896671295166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.671
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.516
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.135
CYP3A4-substrate:	0.074

ADMET: Excretion

Clearance (CL):	4.296
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.029
Drug-inuced Liver Injury (DILI):	0.574
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.084
Skin Sensitization:	0.956
Carcinogencity:	0.539
Eye Corrosion:	0.014
Eye Irritation:	0.977
Respiratory Toxicity:	0.574

Download Data

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

Natural Product: NPC228318

Natural Product ID:	NPC228318
*Common Name:**	ISOSGRNBACDIEA-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ISOSGRNBACDIEA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H10O3/c19-17-14-8-4-7-12-9-10-13(11-5-2-1-3-6-11)16(15(12)14)18(20)21-17/h1-10H
SMILES:	c1ccc(cc1)c1ccc2cccc3c2c1C(=O)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593482
PubChem CID:	11818168
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002044] Phenylnaphthalenes

*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
NPO15254	Macropidia fuliginosa	Species	Haemodoraceae	Eukaryota	n.a.	Australian	n.a.	PMID[26151487]
NPO15254	Macropidia fuliginosa	Species	Haemodoraceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	2.0	mm	PMID[506589]

☑ 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 NPC228318 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	457
0.1-0.2	1705
0.2-0.3	3695
0.3-0.4	11090
0.4-0.5	10211
0.5-0.6	10631
0.6-0.7	4564
0.7-0.8	318
0.8-0.85	22
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9099	High Similarity	NPC79496
0.8673	High Similarity	NPC167504
0.8509	High Similarity	NPC210089
0.8496	Intermediate Similarity	NPC318327
0.8417	Intermediate Similarity	NPC232958
0.839	Intermediate Similarity	NPC158157
0.8347	Intermediate Similarity	NPC144547
0.8276	Intermediate Similarity	NPC66208
0.8264	Intermediate Similarity	NPC289432
0.8264	Intermediate Similarity	NPC988
0.822	Intermediate Similarity	NPC474095
0.822	Intermediate Similarity	NPC306740
0.8198	Intermediate Similarity	NPC42211
0.8151	Intermediate Similarity	NPC135730
0.8142	Intermediate Similarity	NPC114594
0.8108	Intermediate Similarity	NPC118343
0.8103	Intermediate Similarity	NPC273837
0.807	Intermediate Similarity	NPC209632
0.807	Intermediate Similarity	NPC105899
0.8053	Intermediate Similarity	NPC255676
0.8051	Intermediate Similarity	NPC128368
0.8036	Intermediate Similarity	NPC70624
0.8031	Intermediate Similarity	NPC428300
0.8	Intermediate Similarity	NPC85511
0.7984	Intermediate Similarity	NPC269923
0.7984	Intermediate Similarity	NPC167323
0.7983	Intermediate Similarity	NPC196673
0.7983	Intermediate Similarity	NPC67377
0.7966	Intermediate Similarity	NPC186128
0.7966	Intermediate Similarity	NPC280789
0.7965	Intermediate Similarity	NPC45613
0.7946	Intermediate Similarity	NPC203925
0.7937	Intermediate Similarity	NPC295664
0.7917	Intermediate Similarity	NPC228936
0.7917	Intermediate Similarity	NPC221275
0.7913	Intermediate Similarity	NPC269457
0.7899	Intermediate Similarity	NPC13784
0.7895	Intermediate Similarity	NPC60679
0.7895	Intermediate Similarity	NPC89886
0.7874	Intermediate Similarity	NPC470765
0.7869	Intermediate Similarity	NPC45794
0.7863	Intermediate Similarity	NPC99846
0.7863	Intermediate Similarity	NPC83628
0.7863	Intermediate Similarity	NPC17417
0.7863	Intermediate Similarity	NPC265407
0.7863	Intermediate Similarity	NPC269023
0.7863	Intermediate Similarity	NPC10251
0.7857	Intermediate Similarity	NPC228739
0.7845	Intermediate Similarity	NPC119271
0.7845	Intermediate Similarity	NPC30594
0.7845	Intermediate Similarity	NPC37622
0.7833	Intermediate Similarity	NPC307651
0.7833	Intermediate Similarity	NPC471721
0.7826	Intermediate Similarity	NPC31786
0.7823	Intermediate Similarity	NPC77000
0.7823	Intermediate Similarity	NPC238861
0.7815	Intermediate Similarity	NPC212415
0.7815	Intermediate Similarity	NPC270699
0.7815	Intermediate Similarity	NPC82899
0.7812	Intermediate Similarity	NPC473220
0.7812	Intermediate Similarity	NPC470753
0.7807	Intermediate Similarity	NPC188895
0.7803	Intermediate Similarity	NPC470406
0.7797	Intermediate Similarity	NPC214067
0.7797	Intermediate Similarity	NPC93084
0.7797	Intermediate Similarity	NPC251854
0.7797	Intermediate Similarity	NPC196246
0.7795	Intermediate Similarity	NPC107846
0.7788	Intermediate Similarity	NPC325497
0.7778	Intermediate Similarity	NPC56493
0.7769	Intermediate Similarity	NPC186933
0.7768	Intermediate Similarity	NPC92754
0.7768	Intermediate Similarity	NPC276775
0.7768	Intermediate Similarity	NPC249912
0.7752	Intermediate Similarity	NPC115797
0.7752	Intermediate Similarity	NPC51448
0.775	Intermediate Similarity	NPC93287
0.7748	Intermediate Similarity	NPC130398
0.7731	Intermediate Similarity	NPC1082
0.7731	Intermediate Similarity	NPC474157
0.7731	Intermediate Similarity	NPC305912
0.7724	Intermediate Similarity	NPC469574
0.7717	Intermediate Similarity	NPC51079
0.7705	Intermediate Similarity	NPC100353
0.7699	Intermediate Similarity	NPC35448
0.7699	Intermediate Similarity	NPC78701
0.7699	Intermediate Similarity	NPC225060
0.7686	Intermediate Similarity	NPC196075
0.7676	Intermediate Similarity	NPC300983
0.7658	Intermediate Similarity	NPC261181
0.7656	Intermediate Similarity	NPC164014
0.7652	Intermediate Similarity	NPC304873
0.7652	Intermediate Similarity	NPC284477
0.7647	Intermediate Similarity	NPC174099
0.7638	Intermediate Similarity	NPC223351
0.7632	Intermediate Similarity	NPC146351
0.7632	Intermediate Similarity	NPC217621
0.7623	Intermediate Similarity	NPC474408
0.7623	Intermediate Similarity	NPC210092
0.7623	Intermediate Similarity	NPC476357
0.7611	Intermediate Similarity	NPC270654
0.7603	Intermediate Similarity	NPC272524
0.7597	Intermediate Similarity	NPC275576
0.7594	Intermediate Similarity	NPC472656
0.7589	Intermediate Similarity	NPC172925
0.7589	Intermediate Similarity	NPC472880
0.7586	Intermediate Similarity	NPC474365
0.7586	Intermediate Similarity	NPC301943
0.7586	Intermediate Similarity	NPC329556
0.7583	Intermediate Similarity	NPC243355
0.7583	Intermediate Similarity	NPC260818
0.7583	Intermediate Similarity	NPC475002
0.7583	Intermediate Similarity	NPC95126
0.7578	Intermediate Similarity	NPC318067
0.7574	Intermediate Similarity	NPC186647
0.7565	Intermediate Similarity	NPC472879
0.7563	Intermediate Similarity	NPC469636
0.7563	Intermediate Similarity	NPC85493
0.7561	Intermediate Similarity	NPC149691
0.7544	Intermediate Similarity	NPC229242
0.7541	Intermediate Similarity	NPC477411
0.7541	Intermediate Similarity	NPC308744
0.7541	Intermediate Similarity	NPC153053
0.754	Intermediate Similarity	NPC473243
0.7538	Intermediate Similarity	NPC169913
0.7538	Intermediate Similarity	NPC51292
0.7537	Intermediate Similarity	NPC329913
0.7537	Intermediate Similarity	NPC126516
0.7521	Intermediate Similarity	NPC158282
0.7521	Intermediate Similarity	NPC321852
0.75	Intermediate Similarity	NPC471832
0.75	Intermediate Similarity	NPC82712
0.75	Intermediate Similarity	NPC57552
0.75	Intermediate Similarity	NPC25458
0.75	Intermediate Similarity	NPC147561
0.748	Intermediate Similarity	NPC50872
0.748	Intermediate Similarity	NPC474685
0.7479	Intermediate Similarity	NPC203732
0.7478	Intermediate Similarity	NPC221825
0.7478	Intermediate Similarity	NPC228435
0.7477	Intermediate Similarity	NPC119631
0.7465	Intermediate Similarity	NPC147250
0.7464	Intermediate Similarity	NPC476191
0.7463	Intermediate Similarity	NPC183103
0.746	Intermediate Similarity	NPC202015
0.746	Intermediate Similarity	NPC204784
0.7458	Intermediate Similarity	NPC134120
0.7456	Intermediate Similarity	NPC253423
0.7447	Intermediate Similarity	NPC308006
0.7445	Intermediate Similarity	NPC472395
0.7445	Intermediate Similarity	NPC472371
0.7444	Intermediate Similarity	NPC470278
0.7444	Intermediate Similarity	NPC72915
0.7438	Intermediate Similarity	NPC291799
0.7438	Intermediate Similarity	NPC474057
0.7419	Intermediate Similarity	NPC226093
0.7413	Intermediate Similarity	NPC119767
0.7407	Intermediate Similarity	NPC48929
0.7407	Intermediate Similarity	NPC203486
0.7405	Intermediate Similarity	NPC177925
0.7402	Intermediate Similarity	NPC243059
0.7402	Intermediate Similarity	NPC280827
0.7394	Intermediate Similarity	NPC478166
0.7385	Intermediate Similarity	NPC236189
0.7381	Intermediate Similarity	NPC254233
0.7377	Intermediate Similarity	NPC474689
0.7376	Intermediate Similarity	NPC66593
0.7372	Intermediate Similarity	NPC283375
0.7372	Intermediate Similarity	NPC183122
0.7368	Intermediate Similarity	NPC61944
0.7364	Intermediate Similarity	NPC472703
0.7345	Intermediate Similarity	NPC289883
0.7344	Intermediate Similarity	NPC472981
0.7339	Intermediate Similarity	NPC318107
0.7338	Intermediate Similarity	NPC213567
0.7333	Intermediate Similarity	NPC249811
0.7328	Intermediate Similarity	NPC9180
0.7328	Intermediate Similarity	NPC100402
0.7324	Intermediate Similarity	NPC27798
0.7324	Intermediate Similarity	NPC93241
0.7324	Intermediate Similarity	NPC260152
0.7319	Intermediate Similarity	NPC210591
0.7319	Intermediate Similarity	NPC214550
0.7319	Intermediate Similarity	NPC62272
0.7319	Intermediate Similarity	NPC475652
0.7315	Intermediate Similarity	NPC296044
0.7315	Intermediate Similarity	NPC167098
0.7308	Intermediate Similarity	NPC472704
0.7308	Intermediate Similarity	NPC328107
0.7305	Intermediate Similarity	NPC69755
0.7304	Intermediate Similarity	NPC226041
0.7297	Intermediate Similarity	NPC472835
0.7295	Intermediate Similarity	NPC265513
0.7279	Intermediate Similarity	NPC225051
0.7279	Intermediate Similarity	NPC474608
0.7273	Intermediate Similarity	NPC253681
0.7273	Intermediate Similarity	NPC474364
0.7266	Intermediate Similarity	NPC48017
0.7266	Intermediate Similarity	NPC4341
0.7266	Intermediate Similarity	NPC476094

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 NPC228318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	939
0.2-0.3	1127
0.3-0.4	2950
0.4-0.5	2347
0.5-0.6	1056
0.6-0.7	275
0.7-0.8	37
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
0.8376	Intermediate Similarity	NPD5951	Approved
0.8333	Intermediate Similarity	NPD7008	Discontinued
0.8264	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1238	Approved
0.8047	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD2182	Approved
0.7826	Intermediate Similarity	NPD164	Approved
0.7823	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1202	Approved
0.7609	Intermediate Similarity	NPD7003	Approved
0.7589	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1929	Approved
0.7586	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1930	Approved
0.7576	Intermediate Similarity	NPD3764	Approved
0.7559	Intermediate Similarity	NPD6287	Discontinued
0.7522	Intermediate Similarity	NPD1989	Approved
0.7518	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1932	Approved
0.7431	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD1281	Approved
0.7417	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD9257	Approved
0.7339	Intermediate Similarity	NPD9259	Approved
0.7321	Intermediate Similarity	NPD1239	Approved
0.7319	Intermediate Similarity	NPD5406	Approved
0.7319	Intermediate Similarity	NPD5405	Approved
0.7319	Intermediate Similarity	NPD5404	Approved
0.7319	Intermediate Similarity	NPD5408	Approved
0.7266	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7713	Phase 3
0.7252	Intermediate Similarity	NPD1283	Approved
0.7239	Intermediate Similarity	NPD6966	Discovery
0.7227	Intermediate Similarity	NPD5909	Discontinued
0.7193	Intermediate Similarity	NPD1563	Approved
0.7192	Intermediate Similarity	NPD3226	Approved
0.7185	Intermediate Similarity	NPD2313	Discontinued
0.7179	Intermediate Similarity	NPD2066	Phase 3
0.7131	Intermediate Similarity	NPD2329	Discontinued
0.7122	Intermediate Similarity	NPD3748	Approved
0.7099	Intermediate Similarity	NPD4878	Approved
0.7099	Intermediate Similarity	NPD3972	Approved
0.708	Intermediate Similarity	NPD4307	Phase 2
0.708	Intermediate Similarity	NPD9258	Approved
0.708	Intermediate Similarity	NPD2979	Phase 3
0.708	Intermediate Similarity	NPD9256	Approved
0.7077	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1651	Approved
0.7042	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7236	Approved
0.7009	Intermediate Similarity	NPD1564	Approved
0.7009	Intermediate Similarity	NPD1565	Approved
0.7009	Intermediate Similarity	NPD1566	Phase 3
0.7009	Intermediate Similarity	NPD3495	Discontinued
0.6992	Remote Similarity	NPD1876	Approved
0.6986	Remote Similarity	NPD6273	Approved
0.6964	Remote Similarity	NPD1087	Approved
0.6959	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1237	Approved
0.694	Remote Similarity	NPD3266	Approved
0.694	Remote Similarity	NPD3267	Approved
0.6929	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6858	Approved
0.6905	Remote Similarity	NPD7094	Approved
0.6894	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1201	Approved
0.6892	Remote Similarity	NPD7239	Suspended
0.6889	Remote Similarity	NPD2798	Approved
0.6879	Remote Similarity	NPD2799	Discontinued
0.6879	Remote Similarity	NPD4308	Phase 3
0.6875	Remote Similarity	NPD4198	Discontinued
0.6875	Remote Similarity	NPD3750	Approved
0.687	Remote Similarity	NPD17	Approved
0.6846	Remote Similarity	NPD7458	Discontinued
0.6838	Remote Similarity	NPD9260	Approved
0.6835	Remote Similarity	NPD3373	Approved
0.6831	Remote Similarity	NPD2438	Suspended
0.6831	Remote Similarity	NPD2531	Phase 2
0.6818	Remote Similarity	NPD4879	Approved
0.6815	Remote Similarity	NPD1470	Approved
0.6815	Remote Similarity	NPD1164	Approved
0.6794	Remote Similarity	NPD5691	Approved
0.6792	Remote Similarity	NPD5844	Phase 1
0.6783	Remote Similarity	NPD1090	Approved
0.6783	Remote Similarity	NPD1471	Phase 3
0.6783	Remote Similarity	NPD1089	Approved
0.6783	Remote Similarity	NPD1086	Approved
0.6767	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1611	Approved
0.6765	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD8032	Phase 2
0.6759	Remote Similarity	NPD4628	Phase 3
0.6755	Remote Similarity	NPD7411	Suspended
0.6753	Remote Similarity	NPD3749	Approved
0.675	Remote Similarity	NPD7798	Approved
0.6746	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5667	Approved
0.6738	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7177	Discontinued
0.6724	Remote Similarity	NPD7609	Phase 3
0.6718	Remote Similarity	NPD9545	Approved
0.6716	Remote Similarity	NPD1608	Approved
0.6709	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD9490	Approved
0.6696	Remote Similarity	NPD800	Approved
0.6693	Remote Similarity	NPD9508	Approved
0.6692	Remote Similarity	NPD1889	Phase 1
0.6691	Remote Similarity	NPD3268	Approved
0.6691	Remote Similarity	NPD2797	Approved
0.6689	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD650	Approved
0.6667	Remote Similarity	NPD5240	Approved
0.6667	Remote Similarity	NPD5239	Approved
0.6667	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD5236	Approved
0.6667	Remote Similarity	NPD5237	Approved
0.6667	Remote Similarity	NPD7631	Approved
0.6667	Remote Similarity	NPD7611	Approved
0.6667	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD5235	Approved
0.6667	Remote Similarity	NPD1088	Approved
0.6641	Remote Similarity	NPD7610	Discontinued
0.664	Remote Similarity	NPD2342	Discontinued
0.6619	Remote Similarity	NPD6039	Approved
0.6618	Remote Similarity	NPD2198	Approved
0.6618	Remote Similarity	NPD2199	Approved
0.6617	Remote Similarity	NPD2345	Approved
0.6617	Remote Similarity	NPD5836	Discontinued
0.6617	Remote Similarity	NPD5125	Phase 3
0.6617	Remote Similarity	NPD4626	Approved
0.6617	Remote Similarity	NPD5126	Approved
0.6607	Remote Similarity	NPD9491	Approved
0.6606	Remote Similarity	NPD225	Approved
0.6606	Remote Similarity	NPD227	Approved
0.6604	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7427	Discontinued
0.6599	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2935	Discontinued
0.6593	Remote Similarity	NPD6637	Approved
0.6591	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6010	Discontinued
0.6589	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6232	Discontinued
0.6581	Remote Similarity	NPD7768	Phase 2
0.6579	Remote Similarity	NPD6585	Discontinued
0.6577	Remote Similarity	NPD942	Approved
0.6569	Remote Similarity	NPD1203	Approved
0.6565	Remote Similarity	NPD9493	Approved
0.6555	Remote Similarity	NPD1693	Approved
0.6552	Remote Similarity	NPD2344	Approved
0.6549	Remote Similarity	NPD1933	Approved
0.6536	Remote Similarity	NPD5890	Approved
0.6536	Remote Similarity	NPD5889	Approved
0.6535	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD2067	Discontinued
0.6531	Remote Similarity	NPD8166	Discontinued
0.6529	Remote Similarity	NPD5926	Approved
0.6528	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7715	Approved
0.6525	Remote Similarity	NPD7714	Approved
0.6525	Remote Similarity	NPD7961	Discontinued
0.6525	Remote Similarity	NPD1508	Approved
0.6522	Remote Similarity	NPD4980	Approved
0.6516	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2347	Approved
0.6512	Remote Similarity	NPD5535	Approved
0.651	Remote Similarity	NPD7390	Discontinued
0.6507	Remote Similarity	NPD2897	Discontinued
0.6496	Remote Similarity	NPD1888	Phase 1
0.6496	Remote Similarity	NPD3225	Approved
0.6496	Remote Similarity	NPD3673	Approved
0.6496	Remote Similarity	NPD3672	Approved
0.6489	Remote Similarity	NPD3317	Approved
0.6484	Remote Similarity	NPD2201	Approved
0.6483	Remote Similarity	NPD4476	Approved
0.6483	Remote Similarity	NPD4477	Approved
0.6474	Remote Similarity	NPD7057	Phase 3
0.6474	Remote Similarity	NPD7058	Phase 2
0.6471	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7009	Phase 2
0.6466	Remote Similarity	NPD1894	Discontinued
0.6463	Remote Similarity	NPD1243	Approved
0.6462	Remote Similarity	NPD1241	Discontinued
0.646	Remote Similarity	NPD7473	Discontinued
0.6452	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD9261	Approved
0.6438	Remote Similarity	NPD2353	Approved
0.6438	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD226	Approved
0.6418	Remote Similarity	NPD4105	Approved
0.6418	Remote Similarity	NPD3024	Approved
0.6418	Remote Similarity	NPD4102	Approved
0.6418	Remote Similarity	NPD3025	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