NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.06
Volume:	256.396
LogP:	2.496
LogD:	2.314
LogS:	-4.131
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.849
Synthetic Accessibility Score:	2.358
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	2.010604293900542e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.223
Plasma Protein Binding (PPB):	97.76226806640625%
Volume Distribution (VD):	0.485
Pgp-substrate:	1.8335329294204712%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.774
CYP2C19-inhibitor:	0.853
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.749
CYP2C9-substrate:	0.843
CYP2D6-inhibitor:	0.834
CYP2D6-substrate:	0.445
CYP3A4-inhibitor:	0.926
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	7.76
Half-life (T1/2):	0.538

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.704
Drug-inuced Liver Injury (DILI):	0.858
AMES Toxicity:	0.914
Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.919
Carcinogencity:	0.921
Eye Corrosion:	0.016
Eye Irritation:	0.964
Respiratory Toxicity:	0.4

Download Data

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

Natural Product: NPC27659

Natural Product ID:	NPC27659
*Common Name:**	Gnf-Pf-2961
IUPAC Name:	7-hydroxy-2-methoxyphenanthrene-1,4-dione
Synonyms:	GNF-Pf-2961
Standard InCHIKey:	FVUZCFUZMSCPCK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O4/c1-19-13-7-12(17)14-10-5-3-9(16)6-8(10)2-4-11(14)15(13)18/h2-7,16H,1H3
SMILES:	COC1=CC(=O)c2c(C1=O)ccc1c2ccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL582103
PubChem CID:	637413
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22466953]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24450804]
NPO7428	Bletilla formosana	Species	Orchidaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[27525452]
NPO7428	Bletilla formosana	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7428	Bletilla formosana	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14362	Orbignya cohune	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7517	Coleus aromaticus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3954	Lanaria lanata	Species	Lanariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2375	Centaurea sphaerocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7428	Bletilla formosana	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12839	Gomphus purpuraceus	Species	Gomphidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8567	Lecanora chlarotera	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23639	Cynanchum viminale	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3110	Selaginella labordei	Species	Selaginellaceae	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
EC50	2
IC50	3
Others	2

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1229	Cell Line	Huh-7	Homo sapiens	CC50	>	10000.0	nM	PMID[572698]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	13850.0	nM	PMID[572700]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	767.0	nM	PMID[572698]
NPT2	Others	Unspecified		IFI	=	7.018	%	PMID[572698]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	215.1	nM	PMID[572698]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[572699]

☑ 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 NPC27659 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	319
0.1-0.2	1596
0.2-0.3	3492
0.3-0.4	10062
0.4-0.5	8838
0.5-0.6	5383
0.6-0.7	9295
0.7-0.8	3403
0.8-0.85	240
0.85-0.9	65
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9462	High Similarity	NPC264022
0.9194	High Similarity	NPC164947
0.8947	High Similarity	NPC475549
0.8923	High Similarity	NPC198305
0.8915	High Similarity	NPC96024
0.8898	High Similarity	NPC164014
0.8898	High Similarity	NPC474766
0.8889	High Similarity	NPC91478
0.8819	High Similarity	NPC135062
0.881	High Similarity	NPC120545
0.8797	High Similarity	NPC50924
0.8788	High Similarity	NPC309430
0.8769	High Similarity	NPC237225
0.876	High Similarity	NPC15837
0.8759	High Similarity	NPC110810
0.8712	High Similarity	NPC93015
0.8712	High Similarity	NPC244699
0.8702	High Similarity	NPC171460
0.8682	High Similarity	NPC123506
0.8676	High Similarity	NPC475104
0.8667	High Similarity	NPC38158
0.8662	High Similarity	NPC80370
0.8652	High Similarity	NPC58373
0.8643	High Similarity	NPC478160
0.8633	High Similarity	NPC478164
0.8615	High Similarity	NPC51037
0.8615	High Similarity	NPC254492
0.8605	High Similarity	NPC199273
0.8601	High Similarity	NPC295977
0.8601	High Similarity	NPC58310
0.8594	High Similarity	NPC282577
0.8593	High Similarity	NPC22644
0.8593	High Similarity	NPC283088
0.8582	High Similarity	NPC53896
0.8582	High Similarity	NPC52407
0.8582	High Similarity	NPC254603
0.8582	High Similarity	NPC171968
0.8561	High Similarity	NPC99731
0.8561	High Similarity	NPC201297
0.8561	High Similarity	NPC146647
0.8561	High Similarity	NPC276238
0.8561	High Similarity	NPC34414
0.855	High Similarity	NPC72667
0.8542	High Similarity	NPC230848
0.8496	Intermediate Similarity	NPC55949
0.8496	Intermediate Similarity	NPC136588
0.8496	Intermediate Similarity	NPC199253
0.8485	Intermediate Similarity	NPC282923
0.8485	Intermediate Similarity	NPC234175
0.8485	Intermediate Similarity	NPC165257
0.8485	Intermediate Similarity	NPC48248
0.848	Intermediate Similarity	NPC28951
0.848	Intermediate Similarity	NPC325646
0.8478	Intermediate Similarity	NPC470407
0.8473	Intermediate Similarity	NPC231774
0.8467	Intermediate Similarity	NPC186647
0.8462	Intermediate Similarity	NPC142956
0.8462	Intermediate Similarity	NPC310540
0.845	Intermediate Similarity	NPC307174
0.8444	Intermediate Similarity	NPC78307
0.8444	Intermediate Similarity	NPC225051
0.8444	Intermediate Similarity	NPC59459
0.8414	Intermediate Similarity	NPC306011
0.8414	Intermediate Similarity	NPC472838
0.8409	Intermediate Similarity	NPC176130
0.8409	Intermediate Similarity	NPC78364
0.8409	Intermediate Similarity	NPC69424
0.8409	Intermediate Similarity	NPC84672
0.8406	Intermediate Similarity	NPC173980
0.8394	Intermediate Similarity	NPC471670
0.8385	Intermediate Similarity	NPC375356
0.8385	Intermediate Similarity	NPC273683
0.837	Intermediate Similarity	NPC183103
0.837	Intermediate Similarity	NPC70622
0.8358	Intermediate Similarity	NPC253488
0.8358	Intermediate Similarity	NPC31799
0.8346	Intermediate Similarity	NPC328694
0.8333	Intermediate Similarity	NPC160499
0.8333	Intermediate Similarity	NPC177925
0.8333	Intermediate Similarity	NPC3224
0.8333	Intermediate Similarity	NPC53414
0.8333	Intermediate Similarity	NPC36868
0.8333	Intermediate Similarity	NPC475957
0.8333	Intermediate Similarity	NPC53206
0.8321	Intermediate Similarity	NPC173978
0.8321	Intermediate Similarity	NPC80035
0.8321	Intermediate Similarity	NPC258502
0.831	Intermediate Similarity	NPC29932
0.8309	Intermediate Similarity	NPC314048
0.8308	Intermediate Similarity	NPC176208
0.8308	Intermediate Similarity	NPC300274
0.8306	Intermediate Similarity	NPC231717
0.8298	Intermediate Similarity	NPC69755
0.8296	Intermediate Similarity	NPC205992
0.8296	Intermediate Similarity	NPC474517
0.8296	Intermediate Similarity	NPC471851
0.8296	Intermediate Similarity	NPC72669
0.8284	Intermediate Similarity	NPC278928
0.8273	Intermediate Similarity	NPC416
0.8273	Intermediate Similarity	NPC13715
0.8273	Intermediate Similarity	NPC61398
0.8273	Intermediate Similarity	NPC4214
0.8271	Intermediate Similarity	NPC428300
0.8271	Intermediate Similarity	NPC324209
0.8264	Intermediate Similarity	NPC472135
0.8261	Intermediate Similarity	NPC155211
0.8261	Intermediate Similarity	NPC86524
0.8261	Intermediate Similarity	NPC254847
0.8258	Intermediate Similarity	NPC103540
0.8248	Intermediate Similarity	NPC202225
0.824	Intermediate Similarity	NPC11824
0.8239	Intermediate Similarity	NPC66593
0.8235	Intermediate Similarity	NPC88864
0.8235	Intermediate Similarity	NPC477407
0.8235	Intermediate Similarity	NPC58685
0.8231	Intermediate Similarity	NPC154696
0.8222	Intermediate Similarity	NPC108129
0.8217	Intermediate Similarity	NPC285829
0.8217	Intermediate Similarity	NPC206778
0.8214	Intermediate Similarity	NPC114620
0.8214	Intermediate Similarity	NPC1268
0.8214	Intermediate Similarity	NPC103337
0.8214	Intermediate Similarity	NPC138099
0.8214	Intermediate Similarity	NPC26924
0.8214	Intermediate Similarity	NPC242994
0.8209	Intermediate Similarity	NPC3009
0.8207	Intermediate Similarity	NPC472841
0.8201	Intermediate Similarity	NPC53001
0.8201	Intermediate Similarity	NPC290601
0.8201	Intermediate Similarity	NPC471905
0.82	Intermediate Similarity	NPC104876
0.82	Intermediate Similarity	NPC245891
0.8195	Intermediate Similarity	NPC96915
0.8194	Intermediate Similarity	NPC136878
0.8188	Intermediate Similarity	NPC288353
0.8182	Intermediate Similarity	NPC472836
0.8182	Intermediate Similarity	NPC471906
0.8182	Intermediate Similarity	NPC79627
0.8182	Intermediate Similarity	NPC193703
0.8182	Intermediate Similarity	NPC21599
0.8175	Intermediate Similarity	NPC477139
0.8175	Intermediate Similarity	NPC294226
0.8175	Intermediate Similarity	NPC193169
0.8175	Intermediate Similarity	NPC115458
0.8175	Intermediate Similarity	NPC267205
0.8175	Intermediate Similarity	NPC263817
0.8175	Intermediate Similarity	NPC4170
0.8169	Intermediate Similarity	NPC19631
0.8169	Intermediate Similarity	NPC308572
0.8169	Intermediate Similarity	NPC239136
0.8162	Intermediate Similarity	NPC205360
0.8162	Intermediate Similarity	NPC85342
0.8162	Intermediate Similarity	NPC41847
0.8156	Intermediate Similarity	NPC315578
0.8156	Intermediate Similarity	NPC181560
0.8156	Intermediate Similarity	NPC169452
0.8154	Intermediate Similarity	NPC259703
0.8154	Intermediate Similarity	NPC190971
0.8154	Intermediate Similarity	NPC216216
0.8154	Intermediate Similarity	NPC32322
0.8148	Intermediate Similarity	NPC303910
0.8145	Intermediate Similarity	NPC21162
0.8143	Intermediate Similarity	NPC87723
0.8143	Intermediate Similarity	NPC230811
0.8138	Intermediate Similarity	NPC478163
0.8129	Intermediate Similarity	NPC474311
0.8129	Intermediate Similarity	NPC474813
0.8129	Intermediate Similarity	NPC315275
0.8129	Intermediate Similarity	NPC141934
0.8125	Intermediate Similarity	NPC478019
0.8125	Intermediate Similarity	NPC28632
0.8116	Intermediate Similarity	NPC288089
0.8116	Intermediate Similarity	NPC44437
0.8116	Intermediate Similarity	NPC274876
0.8116	Intermediate Similarity	NPC12070
0.811	Intermediate Similarity	NPC322197
0.8102	Intermediate Similarity	NPC312560
0.8099	Intermediate Similarity	NPC246638
0.8099	Intermediate Similarity	NPC305845
0.8099	Intermediate Similarity	NPC204045
0.8099	Intermediate Similarity	NPC124365
0.8095	Intermediate Similarity	NPC196673
0.8092	Intermediate Similarity	NPC295034
0.8088	Intermediate Similarity	NPC117609
0.8088	Intermediate Similarity	NPC475741
0.8085	Intermediate Similarity	NPC190457
0.8085	Intermediate Similarity	NPC477408
0.8085	Intermediate Similarity	NPC143438
0.8071	Intermediate Similarity	NPC471452
0.8071	Intermediate Similarity	NPC245923
0.8071	Intermediate Similarity	NPC305060
0.8071	Intermediate Similarity	NPC119542
0.8062	Intermediate Similarity	NPC318173
0.806	Intermediate Similarity	NPC474737
0.806	Intermediate Similarity	NPC1991
0.806	Intermediate Similarity	NPC306765
0.806	Intermediate Similarity	NPC71610
0.8058	Intermediate Similarity	NPC153088
0.8058	Intermediate Similarity	NPC249272
0.8056	Intermediate Similarity	NPC48762

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 NPC27659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	986
0.2-0.3	1204
0.3-0.4	2516
0.4-0.5	2302
0.5-0.6	1240
0.6-0.7	509
0.7-0.8	87
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1470	Approved
0.8092	Intermediate Similarity	NPD1201	Approved
0.8045	Intermediate Similarity	NPD1283	Approved
0.8	Intermediate Similarity	NPD1651	Approved
0.7939	Intermediate Similarity	NPD2932	Approved
0.7907	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1281	Approved
0.7817	Intermediate Similarity	NPD5408	Approved
0.7817	Intermediate Similarity	NPD5405	Approved
0.7817	Intermediate Similarity	NPD5404	Approved
0.7817	Intermediate Similarity	NPD5406	Approved
0.7803	Intermediate Similarity	NPD3019	Approved
0.7724	Intermediate Similarity	NPD7003	Approved
0.7687	Intermediate Similarity	NPD7390	Discontinued
0.7647	Intermediate Similarity	NPD1876	Approved
0.7639	Intermediate Similarity	NPD2346	Discontinued
0.763	Intermediate Similarity	NPD3972	Approved
0.7591	Intermediate Similarity	NPD1164	Approved
0.7571	Intermediate Similarity	NPD3764	Approved
0.7569	Intermediate Similarity	NPD2935	Discontinued
0.755	Intermediate Similarity	NPD3226	Approved
0.7517	Intermediate Similarity	NPD1471	Phase 3
0.7483	Intermediate Similarity	NPD1607	Approved
0.7481	Intermediate Similarity	NPD5951	Approved
0.7463	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2344	Approved
0.7383	Intermediate Similarity	NPD3300	Phase 2
0.7381	Intermediate Similarity	NPD1237	Approved
0.7379	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1510	Phase 2
0.7365	Intermediate Similarity	NPD8166	Discontinued
0.7365	Intermediate Similarity	NPD3750	Approved
0.7358	Intermediate Similarity	NPD6232	Discontinued
0.7353	Intermediate Similarity	NPD3023	Approved
0.7353	Intermediate Similarity	NPD3026	Approved
0.7344	Intermediate Similarity	NPD2342	Discontinued
0.7343	Intermediate Similarity	NPD1240	Approved
0.7343	Intermediate Similarity	NPD2979	Phase 3
0.7343	Intermediate Similarity	NPD943	Approved
0.7333	Intermediate Similarity	NPD3024	Approved
0.7333	Intermediate Similarity	NPD3025	Approved
0.7329	Intermediate Similarity	NPD7473	Discontinued
0.732	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7458	Discontinued
0.7297	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD6663	Approved
0.726	Intermediate Similarity	NPD2799	Discontinued
0.726	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9545	Approved
0.7252	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7244	Intermediate Similarity	NPD7819	Suspended
0.7237	Intermediate Similarity	NPD6273	Approved
0.7234	Intermediate Similarity	NPD5736	Approved
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7209	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2309	Approved
0.7197	Intermediate Similarity	NPD7635	Approved
0.7188	Intermediate Similarity	NPD6959	Discontinued
0.7163	Intermediate Similarity	NPD2798	Approved
0.7153	Intermediate Similarity	NPD2286	Discontinued
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7133	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7008	Discontinued
0.7114	Intermediate Similarity	NPD1549	Phase 2
0.7114	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD9494	Approved
0.7107	Intermediate Similarity	NPD7075	Discontinued
0.7095	Intermediate Similarity	NPD2438	Suspended
0.7095	Intermediate Similarity	NPD2531	Phase 2
0.7083	Intermediate Similarity	NPD2313	Discontinued
0.7071	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3020	Approved
0.7047	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1930	Approved
0.7031	Intermediate Similarity	NPD1929	Approved
0.703	Intermediate Similarity	NPD5844	Phase 1
0.7027	Intermediate Similarity	NPD4308	Phase 3
0.7027	Intermediate Similarity	NPD3748	Approved
0.7025	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1512	Approved
0.7007	Intermediate Similarity	NPD3091	Approved
0.7	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD4878	Approved
0.6985	Remote Similarity	NPD9493	Approved
0.6978	Remote Similarity	NPD4879	Approved
0.6974	Remote Similarity	NPD2354	Approved
0.697	Remote Similarity	NPD3022	Approved
0.697	Remote Similarity	NPD3021	Approved
0.696	Remote Similarity	NPD2859	Approved
0.696	Remote Similarity	NPD2860	Approved
0.6957	Remote Similarity	NPD5691	Approved
0.6953	Remote Similarity	NPD1932	Approved
0.6948	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2532	Approved
0.6948	Remote Similarity	NPD2533	Approved
0.6948	Remote Similarity	NPD2534	Approved
0.6943	Remote Similarity	NPD4380	Phase 2
0.6943	Remote Similarity	NPD6599	Discontinued
0.6937	Remote Similarity	NPD3882	Suspended
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD288	Approved
0.6897	Remote Similarity	NPD7095	Approved
0.6883	Remote Similarity	NPD1511	Approved
0.688	Remote Similarity	NPD2933	Approved
0.688	Remote Similarity	NPD2934	Approved
0.6875	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7177	Discontinued
0.6863	Remote Similarity	NPD6190	Approved
0.6855	Remote Similarity	NPD6801	Discontinued
0.6855	Remote Similarity	NPD1934	Approved
0.6853	Remote Similarity	NPD1203	Approved
0.6849	Remote Similarity	NPD3268	Approved
0.6849	Remote Similarity	NPD6798	Discontinued
0.6838	Remote Similarity	NPD497	Approved
0.6838	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7768	Phase 2
0.6831	Remote Similarity	NPD1755	Approved
0.6825	Remote Similarity	NPD844	Approved
0.6824	Remote Similarity	NPD6355	Discontinued
0.6824	Remote Similarity	NPD230	Phase 1
0.6821	Remote Similarity	NPD2353	Approved
0.6821	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7236	Approved
0.6812	Remote Similarity	NPD5536	Phase 2
0.6809	Remote Similarity	NPD1611	Approved
0.6809	Remote Similarity	NPD3092	Approved
0.6803	Remote Similarity	NPD8032	Phase 2
0.6802	Remote Similarity	NPD8150	Discontinued
0.6797	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5049	Phase 3
0.6792	Remote Similarity	NPD7411	Suspended
0.679	Remote Similarity	NPD3749	Approved
0.6786	Remote Similarity	NPD4059	Approved
0.6786	Remote Similarity	NPD3095	Discontinued
0.6786	Remote Similarity	NPD17	Approved
0.6781	Remote Similarity	NPD4625	Phase 3
0.6774	Remote Similarity	NPD6799	Approved
0.6774	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD74	Approved
0.6767	Remote Similarity	NPD9266	Approved
0.6767	Remote Similarity	NPD2329	Discontinued
0.6765	Remote Similarity	NPD495	Approved
0.6765	Remote Similarity	NPD498	Approved
0.6765	Remote Similarity	NPD496	Approved
0.6761	Remote Similarity	NPD9269	Phase 2
0.6761	Remote Similarity	NPD1481	Phase 2
0.6757	Remote Similarity	NPD4307	Phase 2
0.6755	Remote Similarity	NPD4476	Approved
0.6755	Remote Similarity	NPD6099	Approved
0.6755	Remote Similarity	NPD2796	Approved
0.6755	Remote Similarity	NPD6100	Approved
0.6755	Remote Similarity	NPD4477	Approved
0.6755	Remote Similarity	NPD1551	Phase 2
0.6753	Remote Similarity	NPD3887	Approved
0.6747	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3094	Phase 2
0.6736	Remote Similarity	NPD2797	Approved
0.6735	Remote Similarity	NPD411	Approved
0.673	Remote Similarity	NPD7028	Phase 2
0.6725	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD164	Approved
0.6714	Remote Similarity	NPD4093	Discontinued
0.6714	Remote Similarity	NPD9268	Approved
0.6713	Remote Similarity	NPD1669	Approved
0.671	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7239	Suspended
0.6708	Remote Similarity	NPD2801	Approved
0.6708	Remote Similarity	NPD1465	Phase 2
0.6706	Remote Similarity	NPD6559	Discontinued
0.6692	Remote Similarity	NPD9263	Approved
0.6692	Remote Similarity	NPD9264	Approved
0.6692	Remote Similarity	NPD9267	Approved
0.669	Remote Similarity	NPD1535	Discovery
0.6689	Remote Similarity	NPD7961	Discontinued
0.6689	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD2296	Approved
0.6667	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD2066	Phase 3
0.6647	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6167	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