NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.06
Volume:	218.338
LogP:	1.881
LogD:	1.73
LogS:	-2.889
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.779
Synthetic Accessibility Score:	2.439
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.675
MDCK Permeability:	1.8457074475008994e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.067

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	92.24539184570312%
Volume Distribution (VD):	0.437
Pgp-substrate:	5.1679792404174805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.802
CYP2C19-inhibitor:	0.551
CYP2C19-substrate:	0.155
CYP2C9-inhibitor:	0.63
CYP2C9-substrate:	0.763
CYP2D6-inhibitor:	0.761
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.639
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	8.172
Half-life (T1/2):	0.691

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.37
AMES Toxicity:	0.786
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.833
Skin Sensitization:	0.822
Carcinogencity:	0.76
Eye Corrosion:	0.117
Eye Irritation:	0.982
Respiratory Toxicity:	0.768

Download Data

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

Natural Product: NPC84273

Natural Product ID:	NPC84273
*Common Name:**	7-Hydroxy-8-Methoxy-2-Methylnaphthalene-1,4-Dione
IUPAC Name:	7-hydroxy-8-methoxy-2-methylnaphthalene-1,4-dione
Synonyms:
Standard InCHIKey:	OBSWMSHOSJMLMV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H10O4/c1-6-5-9(14)7-3-4-8(13)12(16-2)10(7)11(6)15/h3-5,13H,1-2H3
SMILES:	COc1c(O)ccc2c1C(=O)C(=CC2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071233
PubChem CID:	70690993
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO32707	burman diospyros burmanica	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22858297]

☑ 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
IC50	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	96000.0	nM	PMID[452635]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	93000.0	nM	PMID[452635]
NPT2	Others	Unspecified		Ratio IC50	=	1.03	n.a.	PMID[452635]

☑ 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 NPC84273 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	374
0.1-0.2	1702
0.2-0.3	4631
0.3-0.4	11269
0.4-0.5	6395
0.5-0.6	3763
0.6-0.7	6671
0.7-0.8	6726
0.8-0.85	991
0.85-0.9	149
0.9-0.95	25
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9568	High Similarity	NPC160777
0.9568	High Similarity	NPC73416
0.9353	High Similarity	NPC11314
0.9306	High Similarity	NPC144283
0.9179	High Similarity	NPC117609
0.9172	High Similarity	NPC302783
0.9172	High Similarity	NPC118427
0.9172	High Similarity	NPC473201
0.9167	High Similarity	NPC134293
0.911	High Similarity	NPC149889
0.911	High Similarity	NPC312338
0.911	High Similarity	NPC164912
0.9044	High Similarity	NPC50763
0.9	High Similarity	NPC223336
0.8955	High Similarity	NPC16651
0.8955	High Similarity	NPC32163
0.8944	High Similarity	NPC169214
0.8944	High Similarity	NPC229218
0.8944	High Similarity	NPC192597
0.8944	High Similarity	NPC141817
0.8944	High Similarity	NPC176030
0.8919	High Similarity	NPC127172
0.8904	High Similarity	NPC37220
0.8897	High Similarity	NPC58373
0.8889	High Similarity	NPC225351
0.8867	High Similarity	NPC178976
0.8859	High Similarity	NPC234485
0.8832	High Similarity	NPC205360
0.8819	High Similarity	NPC142165
0.8808	High Similarity	NPC477410
0.8803	High Similarity	NPC50823
0.88	High Similarity	NPC77807
0.88	High Similarity	NPC5379
0.88	High Similarity	NPC279605
0.88	High Similarity	NPC14561
0.8786	High Similarity	NPC324929
0.8776	High Similarity	NPC237441
0.8767	High Similarity	NPC77598
0.8759	High Similarity	NPC66905
0.875	High Similarity	NPC254659
0.8742	High Similarity	NPC37543
0.8742	High Similarity	NPC199463
0.8716	High Similarity	NPC103509
0.8714	High Similarity	NPC22222
0.8714	High Similarity	NPC281513
0.8705	High Similarity	NPC327410
0.8705	High Similarity	NPC294226
0.8693	High Similarity	NPC311740
0.869	High Similarity	NPC309169
0.869	High Similarity	NPC196941
0.869	High Similarity	NPC475201
0.8686	High Similarity	NPC261759
0.8667	High Similarity	NPC107109
0.8667	High Similarity	NPC474000
0.8662	High Similarity	NPC325625
0.8658	High Similarity	NPC78505
0.8658	High Similarity	NPC75377
0.8658	High Similarity	NPC306011
0.8658	High Similarity	NPC472838
0.8657	High Similarity	NPC182646
0.8645	High Similarity	NPC26386
0.8639	High Similarity	NPC52692
0.8627	High Similarity	NPC84571
0.8621	High Similarity	NPC46161
0.8621	High Similarity	NPC287722
0.8621	High Similarity	NPC50954
0.8621	High Similarity	NPC239608
0.8609	High Similarity	NPC472048
0.8609	High Similarity	NPC38898
0.8593	High Similarity	NPC30216
0.8591	High Similarity	NPC58310
0.8591	High Similarity	NPC31132
0.8591	High Similarity	NPC295977
0.8591	High Similarity	NPC472279
0.8582	High Similarity	NPC258502
0.8582	High Similarity	NPC139519
0.8581	High Similarity	NPC287395
0.8581	High Similarity	NPC183655
0.8571	High Similarity	NPC226987
0.8571	High Similarity	NPC143903
0.8562	High Similarity	NPC229787
0.8562	High Similarity	NPC104876
0.8562	High Similarity	NPC245891
0.8553	High Similarity	NPC213401
0.8552	High Similarity	NPC299154
0.8552	High Similarity	NPC301178
0.8552	High Similarity	NPC284556
0.8552	High Similarity	NPC312256
0.8543	High Similarity	NPC475770
0.8543	High Similarity	NPC305710
0.854	High Similarity	NPC203719
0.854	High Similarity	NPC117237
0.854	High Similarity	NPC473787
0.854	High Similarity	NPC45537
0.8531	High Similarity	NPC61398
0.8531	High Similarity	NPC416
0.8523	High Similarity	NPC142876
0.8523	High Similarity	NPC40290
0.8523	High Similarity	NPC139293
0.8523	High Similarity	NPC102003
0.8523	High Similarity	NPC200060
0.8523	High Similarity	NPC195763
0.8523	High Similarity	NPC264550
0.8523	High Similarity	NPC92722
0.8523	High Similarity	NPC264289
0.8523	High Similarity	NPC69430
0.8523	High Similarity	NPC333691
0.8521	High Similarity	NPC141934
0.8514	High Similarity	NPC188074
0.8514	High Similarity	NPC125449
0.8506	High Similarity	NPC185617
0.8503	High Similarity	NPC478019
0.85	High Similarity	NPC111888
0.8493	Intermediate Similarity	NPC258307
0.8493	Intermediate Similarity	NPC119663
0.8493	Intermediate Similarity	NPC471417
0.8483	Intermediate Similarity	NPC110419
0.8478	Intermediate Similarity	NPC237225
0.8477	Intermediate Similarity	NPC137125
0.8477	Intermediate Similarity	NPC3744
0.8477	Intermediate Similarity	NPC180388
0.8472	Intermediate Similarity	NPC477408
0.8472	Intermediate Similarity	NPC4796
0.8467	Intermediate Similarity	NPC85131
0.8467	Intermediate Similarity	NPC151473
0.8467	Intermediate Similarity	NPC29231
0.8462	Intermediate Similarity	NPC476822
0.8456	Intermediate Similarity	NPC203747
0.8456	Intermediate Similarity	NPC80710
0.8456	Intermediate Similarity	NPC55327
0.8456	Intermediate Similarity	NPC15329
0.8456	Intermediate Similarity	NPC254702
0.8456	Intermediate Similarity	NPC131451
0.8456	Intermediate Similarity	NPC139364
0.8456	Intermediate Similarity	NPC194653
0.8451	Intermediate Similarity	NPC208760
0.8451	Intermediate Similarity	NPC89504
0.8451	Intermediate Similarity	NPC95485
0.8451	Intermediate Similarity	NPC88065
0.8446	Intermediate Similarity	NPC85734
0.8446	Intermediate Similarity	NPC39361
0.8446	Intermediate Similarity	NPC32058
0.8444	Intermediate Similarity	NPC114298
0.844	Intermediate Similarity	NPC283823
0.844	Intermediate Similarity	NPC159418
0.8435	Intermediate Similarity	NPC19896
0.8435	Intermediate Similarity	NPC275278
0.8435	Intermediate Similarity	NPC207732
0.8433	Intermediate Similarity	NPC225245
0.8431	Intermediate Similarity	NPC470762
0.8431	Intermediate Similarity	NPC288353
0.8431	Intermediate Similarity	NPC474167
0.8425	Intermediate Similarity	NPC69755
0.8421	Intermediate Similarity	NPC93552
0.8421	Intermediate Similarity	NPC472905
0.8414	Intermediate Similarity	NPC82336
0.8414	Intermediate Similarity	NPC78987
0.8411	Intermediate Similarity	NPC256406
0.8411	Intermediate Similarity	NPC31363
0.8411	Intermediate Similarity	NPC46882
0.8411	Intermediate Similarity	NPC132990
0.8411	Intermediate Similarity	NPC70320
0.8408	Intermediate Similarity	NPC191930
0.8406	Intermediate Similarity	NPC5018
0.8406	Intermediate Similarity	NPC324209
0.8406	Intermediate Similarity	NPC123228
0.8406	Intermediate Similarity	NPC123722
0.8406	Intermediate Similarity	NPC151167
0.8406	Intermediate Similarity	NPC276466
0.84	Intermediate Similarity	NPC472837
0.8389	Intermediate Similarity	NPC168803
0.8389	Intermediate Similarity	NPC55557
0.8389	Intermediate Similarity	NPC30647
0.8389	Intermediate Similarity	NPC93034
0.8389	Intermediate Similarity	NPC61871
0.8389	Intermediate Similarity	NPC476821
0.8389	Intermediate Similarity	NPC119660
0.8382	Intermediate Similarity	NPC4181
0.8382	Intermediate Similarity	NPC164778
0.8382	Intermediate Similarity	NPC257976
0.8382	Intermediate Similarity	NPC242372
0.8378	Intermediate Similarity	NPC157133
0.8378	Intermediate Similarity	NPC28632
0.8377	Intermediate Similarity	NPC472963
0.8377	Intermediate Similarity	NPC179732
0.8377	Intermediate Similarity	NPC136674
0.8369	Intermediate Similarity	NPC477406
0.8369	Intermediate Similarity	NPC239302
0.8367	Intermediate Similarity	NPC46880
0.8366	Intermediate Similarity	NPC152951
0.8366	Intermediate Similarity	NPC117992
0.8366	Intermediate Similarity	NPC230149
0.8366	Intermediate Similarity	NPC57674
0.8366	Intermediate Similarity	NPC168247
0.8366	Intermediate Similarity	NPC39184
0.8358	Intermediate Similarity	NPC285829
0.8358	Intermediate Similarity	NPC206778
0.8357	Intermediate Similarity	NPC298268
0.8357	Intermediate Similarity	NPC172673
0.8355	Intermediate Similarity	NPC216769

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 NPC84273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	1008
0.2-0.3	1635
0.3-0.4	2699
0.4-0.5	1753
0.5-0.6	1053
0.6-0.7	520
0.7-0.8	125
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.854	High Similarity	NPD9494	Approved
0.8194	Intermediate Similarity	NPD3882	Suspended
0.8182	Intermediate Similarity	NPD2801	Approved
0.8165	Intermediate Similarity	NPD6232	Discontinued
0.8125	Intermediate Similarity	NPD7473	Discontinued
0.8117	Intermediate Similarity	NPD1934	Approved
0.8067	Intermediate Similarity	NPD1511	Approved
0.806	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD447	Suspended
0.8014	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD943	Approved
0.7986	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1512	Approved
0.7949	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2344	Approved
0.7877	Intermediate Similarity	NPD1607	Approved
0.7872	Intermediate Similarity	NPD1470	Approved
0.7862	Intermediate Similarity	NPD1240	Approved
0.7838	Intermediate Similarity	NPD2935	Discontinued
0.7785	Intermediate Similarity	NPD2346	Discontinued
0.777	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1510	Phase 2
0.7765	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2309	Approved
0.7692	Intermediate Similarity	NPD3226	Approved
0.7687	Intermediate Similarity	NPD228	Approved
0.7667	Intermediate Similarity	NPD1471	Phase 3
0.7651	Intermediate Similarity	NPD2799	Discontinued
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.7622	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6166	Phase 2
0.7622	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1465	Phase 2
0.7589	Intermediate Similarity	NPD1201	Approved
0.7568	Intermediate Similarity	NPD230	Phase 1
0.7562	Intermediate Similarity	NPD3817	Phase 2
0.7548	Intermediate Similarity	NPD2534	Approved
0.7548	Intermediate Similarity	NPD2532	Approved
0.7548	Intermediate Similarity	NPD2533	Approved
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD1549	Phase 2
0.7485	Intermediate Similarity	NPD7054	Approved
0.7485	Intermediate Similarity	NPD5494	Approved
0.7482	Intermediate Similarity	NPD5536	Phase 2
0.7448	Intermediate Similarity	NPD2798	Approved
0.744	Intermediate Similarity	NPD7472	Approved
0.744	Intermediate Similarity	NPD7074	Phase 3
0.7436	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1283	Approved
0.7431	Intermediate Similarity	NPD1876	Approved
0.7413	Intermediate Similarity	NPD3972	Approved
0.7413	Intermediate Similarity	NPD9717	Approved
0.741	Intermediate Similarity	NPD9493	Approved
0.7407	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8166	Discontinued
0.7403	Intermediate Similarity	NPD4628	Phase 3
0.7381	Intermediate Similarity	NPD5844	Phase 1
0.7379	Intermediate Similarity	NPD1203	Approved
0.7376	Intermediate Similarity	NPD1651	Approved
0.7372	Intermediate Similarity	NPD6799	Approved
0.7368	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2313	Discontinued
0.7365	Intermediate Similarity	NPD411	Approved
0.7362	Intermediate Similarity	NPD7075	Discontinued
0.7358	Intermediate Similarity	NPD7458	Discontinued
0.7358	Intermediate Similarity	NPD824	Approved
0.7349	Intermediate Similarity	NPD3926	Phase 2
0.7338	Intermediate Similarity	NPD2800	Approved
0.7333	Intermediate Similarity	NPD1933	Approved
0.7333	Intermediate Similarity	NPD1247	Approved
0.7324	Intermediate Similarity	NPD4626	Approved
0.7319	Intermediate Similarity	NPD1241	Discontinued
0.7317	Intermediate Similarity	NPD919	Approved
0.7312	Intermediate Similarity	NPD6599	Discontinued
0.731	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6797	Phase 2
0.729	Intermediate Similarity	NPD3750	Approved
0.729	Intermediate Similarity	NPD7003	Approved
0.7284	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7251	Discontinued
0.7229	Intermediate Similarity	NPD6959	Discontinued
0.7226	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1281	Approved
0.7222	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7808	Phase 3
0.7205	Intermediate Similarity	NPD7028	Phase 2
0.7197	Intermediate Similarity	NPD3300	Phase 2
0.7184	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD9545	Approved
0.7175	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD9269	Phase 2
0.7171	Intermediate Similarity	NPD6651	Approved
0.7152	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD3749	Approved
0.7152	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD2796	Approved
0.7134	Intermediate Similarity	NPD2296	Approved
0.7134	Intermediate Similarity	NPD5978	Approved
0.7134	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5977	Approved
0.7125	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7117	Intermediate Similarity	NPD6801	Discontinued
0.7108	Intermediate Similarity	NPD6234	Discontinued
0.7088	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5283	Phase 1
0.7055	Intermediate Similarity	NPD7411	Suspended
0.705	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7390	Discontinued
0.7037	Intermediate Similarity	NPD2651	Approved
0.7037	Intermediate Similarity	NPD2649	Approved
0.7032	Intermediate Similarity	NPD5404	Approved
0.7032	Intermediate Similarity	NPD5408	Approved
0.7032	Intermediate Similarity	NPD5405	Approved
0.7032	Intermediate Similarity	NPD5406	Approved
0.7027	Intermediate Similarity	NPD1164	Approved
0.702	Intermediate Similarity	NPD3764	Approved
0.7014	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5691	Approved
0.7012	Intermediate Similarity	NPD37	Approved
0.7007	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6832	Phase 2
0.6994	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5711	Approved
0.6982	Remote Similarity	NPD5710	Approved
0.6971	Remote Similarity	NPD8313	Approved
0.6971	Remote Similarity	NPD8312	Approved
0.6968	Remote Similarity	NPD3748	Approved
0.6966	Remote Similarity	NPD2932	Approved
0.6962	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4110	Phase 3
0.6957	Remote Similarity	NPD6273	Approved
0.6954	Remote Similarity	NPD6559	Discontinued
0.6954	Remote Similarity	NPD7685	Pre-registration
0.6954	Remote Similarity	NPD3027	Phase 3
0.6951	Remote Similarity	NPD6386	Approved
0.6951	Remote Similarity	NPD6385	Approved
0.6949	Remote Similarity	NPD8434	Phase 2
0.6949	Remote Similarity	NPD8150	Discontinued
0.6939	Remote Similarity	NPD1608	Approved
0.6933	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3455	Phase 2
0.6928	Remote Similarity	NPD5402	Approved
0.6918	Remote Similarity	NPD2354	Approved
0.6918	Remote Similarity	NPD6190	Approved
0.6914	Remote Similarity	NPD920	Approved
0.6902	Remote Similarity	NPD6780	Approved
0.6902	Remote Similarity	NPD6782	Approved
0.6902	Remote Similarity	NPD6778	Approved
0.6902	Remote Similarity	NPD6777	Approved
0.6902	Remote Similarity	NPD6781	Approved
0.6902	Remote Similarity	NPD6776	Approved
0.6902	Remote Similarity	NPD6779	Approved
0.6901	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1243	Approved
0.6897	Remote Similarity	NPD9268	Approved
0.6887	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7768	Phase 2
0.6886	Remote Similarity	NPD4965	Approved
0.6886	Remote Similarity	NPD4966	Approved
0.6886	Remote Similarity	NPD4967	Phase 2
0.6883	Remote Similarity	NPD6355	Discontinued
0.6879	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1019	Discontinued
0.6859	Remote Similarity	NPD4308	Phase 3
0.6855	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3019	Approved
0.6848	Remote Similarity	NPD6873	Phase 2
0.6835	Remote Similarity	NPD74	Approved
0.6835	Remote Similarity	NPD9266	Approved
0.6824	Remote Similarity	NPD8127	Discontinued
0.6824	Remote Similarity	NPD7199	Phase 2
0.6821	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7228	Approved
0.6818	Remote Similarity	NPD2979	Phase 3
0.6818	Remote Similarity	NPD1613	Approved
0.6818	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6100	Approved
0.6815	Remote Similarity	NPD2438	Suspended
0.6815	Remote Similarity	NPD6099	Approved
0.681	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5403	Approved
0.6807	Remote Similarity	NPD6279	Approved
0.6807	Remote Similarity	NPD6280	Approved
0.6807	Remote Similarity	NPD6844	Discontinued
0.6802	Remote Similarity	NPD2898	Approved
0.68	Remote Similarity	NPD5953	Discontinued

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