NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.08
Volume:	261.72
LogP:	3.052
LogD:	2.413
LogS:	-3.539
# Rotatable Bonds:	3
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.741
Synthetic Accessibility Score:	2.734
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.953
MDCK Permeability:	1.199621783598559e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	96.2102279663086%
Volume Distribution (VD):	0.57
Pgp-substrate:	10.888339042663574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.381
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.797
CYP2D6-inhibitor:	0.291
CYP2D6-substrate:	0.703
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	11.766
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.835
AMES Toxicity:	0.52
Rat Oral Acute Toxicity:	0.372
Maximum Recommended Daily Dose:	0.853
Skin Sensitization:	0.91
Carcinogencity:	0.193
Eye Corrosion:	0.08
Eye Irritation:	0.943
Respiratory Toxicity:	0.679

Download Data

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

Natural Product: NPC28632

Natural Product ID:	NPC28632
*Common Name:**	6-Ethyl-5-Hydroxy-2,7-Dimethoxynaphthalene-1,4-Dione
IUPAC Name:	6-ethyl-5-hydroxy-2,7-dimethoxynaphthalene-1,4-dione
Synonyms:
Standard InCHIKey:	KRSHMRFACGPISX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O5/c1-4-7-10(18-2)5-8-12(14(7)17)9(15)6-11(19-3)13(8)16/h5-6,17H,4H2,1-3H3
SMILES:	CCc1c(cc2c(C(=O)C=C(C2=O)OC)c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204404
PubChem CID:	15061180
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
NPO14117	Diplodia sapinea	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075753]
NPO20359	Hortaea werneckii	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[11374967]
NPO14117	Diplodia sapinea	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24285	Dendrodoris nigra	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24070	Dysphania multifida	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20359	Hortaea werneckii	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24444	Musca domestica	Species	Muscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21609	Neofuscelia loxodella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24174	Zanthoxylum hyemale	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24330	Aconitum firmum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20975	Tiquilia plicata	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8045	Xenophyllum dactylophyllum	Species	Asteraceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	12.5	ug.mL-1	PMID[528730]

☑ 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 NPC28632 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	407
0.1-0.2	1743
0.2-0.3	4336
0.3-0.4	10590
0.4-0.5	7785
0.5-0.6	3996
0.6-0.7	5777
0.7-0.8	5614
0.8-0.85	2021
0.85-0.9	368
0.9-0.95	59
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC80370
0.9306	High Similarity	NPC126767
0.9306	High Similarity	NPC56433
0.9306	High Similarity	NPC118027
0.9306	High Similarity	NPC289042
0.9306	High Similarity	NPC190648
0.9306	High Similarity	NPC312929
0.9306	High Similarity	NPC245584
0.9262	High Similarity	NPC474637
0.9231	High Similarity	NPC475201
0.9231	High Similarity	NPC19896
0.9225	High Similarity	NPC94076
0.9225	High Similarity	NPC182255
0.9184	High Similarity	NPC230848
0.9161	High Similarity	NPC84266
0.9139	High Similarity	NPC313368
0.9116	High Similarity	NPC470568
0.9116	High Similarity	NPC255641
0.9116	High Similarity	NPC294646
0.9116	High Similarity	NPC147735
0.9116	High Similarity	NPC290954
0.9085	High Similarity	NPC165172
0.9054	High Similarity	NPC470569
0.9007	High Similarity	NPC201127
0.9	High Similarity	NPC234485
0.8993	High Similarity	NPC40356
0.8993	High Similarity	NPC154683
0.898	High Similarity	NPC2569
0.898	High Similarity	NPC172329
0.8958	High Similarity	NPC49108
0.8951	High Similarity	NPC156872
0.8947	High Similarity	NPC477410
0.8933	High Similarity	NPC127172
0.8933	High Similarity	NPC208806
0.8933	High Similarity	NPC107109
0.8926	High Similarity	NPC46882
0.8926	High Similarity	NPC132990
0.8921	High Similarity	NPC309430
0.8919	High Similarity	NPC134293
0.8919	High Similarity	NPC198927
0.8912	High Similarity	NPC34802
0.8912	High Similarity	NPC22005
0.8912	High Similarity	NPC7943
0.8912	High Similarity	NPC123202
0.8903	High Similarity	NPC316262
0.8903	High Similarity	NPC314653
0.8897	High Similarity	NPC167663
0.8889	High Similarity	NPC110810
0.8881	High Similarity	NPC25427
0.8874	High Similarity	NPC226656
0.8874	High Similarity	NPC66508
0.8859	High Similarity	NPC103509
0.8859	High Similarity	NPC202595
0.8851	High Similarity	NPC27221
0.8851	High Similarity	NPC7025
0.8851	High Similarity	NPC256672
0.8844	High Similarity	NPC225173
0.8844	High Similarity	NPC163846
0.8841	High Similarity	NPC230818
0.8836	High Similarity	NPC193703
0.8836	High Similarity	NPC48762
0.8836	High Similarity	NPC21599
0.8824	High Similarity	NPC104876
0.8824	High Similarity	NPC245891
0.8824	High Similarity	NPC228654
0.8819	High Similarity	NPC472366
0.8819	High Similarity	NPC49242
0.8819	High Similarity	NPC109007
0.8816	High Similarity	NPC14561
0.8816	High Similarity	NPC5379
0.8816	High Similarity	NPC77807
0.8808	High Similarity	NPC155686
0.8808	High Similarity	NPC214632
0.8803	High Similarity	NPC158481
0.8792	High Similarity	NPC100985
0.8792	High Similarity	NPC4423
0.8792	High Similarity	NPC77325
0.8792	High Similarity	NPC65589
0.8792	High Similarity	NPC97028
0.8792	High Similarity	NPC97029
0.8792	High Similarity	NPC329933
0.8792	High Similarity	NPC158338
0.8792	High Similarity	NPC288036
0.879	High Similarity	NPC95715
0.8786	High Similarity	NPC27490
0.8784	High Similarity	NPC125801
0.8777	High Similarity	NPC84772
0.8776	High Similarity	NPC49282
0.8776	High Similarity	NPC474630
0.8776	High Similarity	NPC473692
0.8776	High Similarity	NPC34482
0.8767	High Similarity	NPC277369
0.8767	High Similarity	NPC215451
0.8766	High Similarity	NPC243701
0.8758	High Similarity	NPC37543
0.8758	High Similarity	NPC199463
0.8758	High Similarity	NPC178976
0.8758	High Similarity	NPC263483
0.8742	High Similarity	NPC470340
0.8733	High Similarity	NPC325983
0.8733	High Similarity	NPC119929
0.8732	High Similarity	NPC182496
0.8732	High Similarity	NPC180905
0.8725	High Similarity	NPC153417
0.8725	High Similarity	NPC472056
0.8725	High Similarity	NPC472841
0.8723	High Similarity	NPC254603
0.8718	High Similarity	NPC476822
0.8716	High Similarity	NPC470570
0.8716	High Similarity	NPC260946
0.8714	High Similarity	NPC324482
0.871	High Similarity	NPC117985
0.871	High Similarity	NPC219686
0.8701	High Similarity	NPC324736
0.8699	High Similarity	NPC126534
0.8699	High Similarity	NPC40118
0.8699	High Similarity	NPC232021
0.8693	High Similarity	NPC180924
0.8693	High Similarity	NPC472050
0.869	High Similarity	NPC477956
0.869	High Similarity	NPC109232
0.8684	High Similarity	NPC93552
0.8681	High Similarity	NPC472419
0.8679	High Similarity	NPC315306
0.8679	High Similarity	NPC313717
0.8675	High Similarity	NPC72958
0.8675	High Similarity	NPC478148
0.8675	High Similarity	NPC258249
0.8675	High Similarity	NPC232645
0.8675	High Similarity	NPC149526
0.8675	High Similarity	NPC474417
0.8671	High Similarity	NPC242712
0.8671	High Similarity	NPC254847
0.8671	High Similarity	NPC50455
0.8667	High Similarity	NPC65775
0.8667	High Similarity	NPC291049
0.8667	High Similarity	NPC10027
0.8667	High Similarity	NPC233267
0.8658	High Similarity	NPC259632
0.8652	High Similarity	NPC88864
0.8645	High Similarity	NPC84571
0.8645	High Similarity	NPC470342
0.8645	High Similarity	NPC472052
0.8645	High Similarity	NPC472060
0.8643	High Similarity	NPC198305
0.8639	High Similarity	NPC297600
0.8639	High Similarity	NPC162476
0.8639	High Similarity	NPC472006
0.8639	High Similarity	NPC310340
0.8636	High Similarity	NPC96342
0.8636	High Similarity	NPC212967
0.8636	High Similarity	NPC164110
0.8636	High Similarity	NPC246647
0.8633	High Similarity	NPC179898
0.863	High Similarity	NPC253822
0.863	High Similarity	NPC265178
0.863	High Similarity	NPC101366
0.863	High Similarity	NPC283292
0.863	High Similarity	NPC11056
0.863	High Similarity	NPC275734
0.8621	High Similarity	NPC52358
0.8621	High Similarity	NPC21350
0.8621	High Similarity	NPC472368
0.8621	High Similarity	NPC1268
0.8621	High Similarity	NPC57380
0.8618	High Similarity	NPC470353
0.8618	High Similarity	NPC149889
0.8618	High Similarity	NPC87708
0.8618	High Similarity	NPC271681
0.8618	High Similarity	NPC312338
0.8618	High Similarity	NPC175978
0.8611	High Similarity	NPC472364
0.8611	High Similarity	NPC168105
0.8611	High Similarity	NPC150399
0.8611	High Similarity	NPC186838
0.8611	High Similarity	NPC41461
0.8611	High Similarity	NPC25287
0.8611	High Similarity	NPC477244
0.8611	High Similarity	NPC135837
0.8611	High Similarity	NPC53206
0.8611	High Similarity	NPC476333
0.8611	High Similarity	NPC98115
0.8611	High Similarity	NPC249606
0.8611	High Similarity	NPC472367
0.8611	High Similarity	NPC274109
0.8611	High Similarity	NPC477242
0.8611	High Similarity	NPC473391
0.8611	High Similarity	NPC12165
0.8611	High Similarity	NPC53414
0.8611	High Similarity	NPC66349
0.8611	High Similarity	NPC477243
0.8611	High Similarity	NPC471905
0.8611	High Similarity	NPC1486
0.8611	High Similarity	NPC193792
0.8609	High Similarity	NPC470107
0.8609	High Similarity	NPC158866
0.8609	High Similarity	NPC150928
0.8601	High Similarity	NPC125920
0.8601	High Similarity	NPC22644
0.8601	High Similarity	NPC164136

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 NPC28632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	1050
0.2-0.3	1776
0.3-0.4	2710
0.4-0.5	1764
0.5-0.6	970
0.6-0.7	341
0.7-0.8	139
0.8-0.85	21
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8671	High Similarity	NPD1509	Clinical (unspecified phase)
0.8662	High Similarity	NPD1607	Approved
0.8621	High Similarity	NPD970	Clinical (unspecified phase)
0.8523	High Similarity	NPD2534	Approved
0.8523	High Similarity	NPD2532	Approved
0.8523	High Similarity	NPD2533	Approved
0.8521	High Similarity	NPD1240	Approved
0.8414	Intermediate Similarity	NPD1510	Phase 2
0.84	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD2800	Approved
0.8302	Intermediate Similarity	NPD6232	Discontinued
0.8261	Intermediate Similarity	NPD7473	Discontinued
0.8239	Intermediate Similarity	NPD6959	Discontinued
0.8205	Intermediate Similarity	NPD7819	Suspended
0.8151	Intermediate Similarity	NPD6651	Approved
0.8121	Intermediate Similarity	NPD1549	Phase 2
0.8101	Intermediate Similarity	NPD3882	Suspended
0.8054	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7075	Discontinued
0.8013	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD1512	Approved
0.7975	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD3226	Approved
0.7922	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6801	Discontinued
0.7898	Intermediate Similarity	NPD4380	Phase 2
0.7895	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3750	Approved
0.7867	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD1511	Approved
0.7857	Intermediate Similarity	NPD7390	Discontinued
0.7857	Intermediate Similarity	NPD6799	Approved
0.7853	Intermediate Similarity	NPD5711	Approved
0.7853	Intermediate Similarity	NPD5710	Approved
0.7812	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD1470	Approved
0.777	Intermediate Similarity	NPD943	Approved
0.775	Intermediate Similarity	NPD2801	Approved
0.7748	Intermediate Similarity	NPD1551	Phase 2
0.7748	Intermediate Similarity	NPD2796	Approved
0.7736	Intermediate Similarity	NPD7411	Suspended
0.7716	Intermediate Similarity	NPD3749	Approved
0.7712	Intermediate Similarity	NPD1243	Approved
0.7707	Intermediate Similarity	NPD920	Approved
0.7701	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1471	Phase 3
0.7697	Intermediate Similarity	NPD2346	Discontinued
0.7683	Intermediate Similarity	NPD1247	Approved
0.7669	Intermediate Similarity	NPD919	Approved
0.7662	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6100	Approved
0.7632	Intermediate Similarity	NPD6099	Approved
0.7593	Intermediate Similarity	NPD3817	Phase 2
0.7582	Intermediate Similarity	NPD2344	Approved
0.7571	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3748	Approved
0.7546	Intermediate Similarity	NPD7768	Phase 2
0.7545	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6166	Phase 2
0.7531	Intermediate Similarity	NPD1465	Phase 2
0.7515	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5494	Approved
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD1201	Approved
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7468	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2799	Discontinued
0.7427	Intermediate Similarity	NPD5953	Discontinued
0.7403	Intermediate Similarity	NPD5406	Approved
0.7403	Intermediate Similarity	NPD5408	Approved
0.7403	Intermediate Similarity	NPD5405	Approved
0.7403	Intermediate Similarity	NPD5404	Approved
0.7394	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2309	Approved
0.7384	Intermediate Similarity	NPD6559	Discontinued
0.7378	Intermediate Similarity	NPD5402	Approved
0.7372	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7353	Intermediate Similarity	NPD3818	Discontinued
0.7347	Intermediate Similarity	NPD1283	Approved
0.7333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6797	Phase 2
0.731	Intermediate Similarity	NPD7286	Phase 2
0.7308	Intermediate Similarity	NPD6779	Approved
0.7308	Intermediate Similarity	NPD6781	Approved
0.7308	Intermediate Similarity	NPD6778	Approved
0.7308	Intermediate Similarity	NPD6782	Approved
0.7308	Intermediate Similarity	NPD6777	Approved
0.7308	Intermediate Similarity	NPD6776	Approved
0.7308	Intermediate Similarity	NPD6780	Approved
0.7292	Intermediate Similarity	NPD1651	Approved
0.7285	Intermediate Similarity	NPD411	Approved
0.7283	Intermediate Similarity	NPD7435	Discontinued
0.7283	Intermediate Similarity	NPD7251	Discontinued
0.7267	Intermediate Similarity	NPD5403	Approved
0.7261	Intermediate Similarity	NPD2654	Approved
0.725	Intermediate Similarity	NPD5401	Approved
0.7248	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7808	Phase 3
0.7241	Intermediate Similarity	NPD4626	Approved
0.7241	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2403	Approved
0.7219	Intermediate Similarity	NPD4625	Phase 3
0.7215	Intermediate Similarity	NPD7003	Approved
0.7215	Intermediate Similarity	NPD4628	Phase 3
0.7211	Intermediate Similarity	NPD9717	Approved
0.7211	Intermediate Similarity	NPD3972	Approved
0.7203	Intermediate Similarity	NPD9493	Approved
0.7191	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7697	Approved
0.7189	Intermediate Similarity	NPD7698	Approved
0.7189	Intermediate Similarity	NPD7696	Phase 3
0.7181	Intermediate Similarity	NPD1203	Approved
0.7175	Intermediate Similarity	NPD8150	Discontinued
0.7171	Intermediate Similarity	NPD2313	Discontinued
0.7171	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7074	Phase 3
0.7162	Intermediate Similarity	NPD4749	Approved
0.7151	Intermediate Similarity	NPD7870	Phase 2
0.7151	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2798	Approved
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1876	Approved
0.711	Intermediate Similarity	NPD7054	Approved
0.7103	Intermediate Similarity	NPD9545	Approved
0.709	Intermediate Similarity	NPD8151	Discontinued
0.7086	Intermediate Similarity	NPD9494	Approved
0.7073	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7458	Discontinued
0.7069	Intermediate Similarity	NPD7472	Approved
0.7067	Intermediate Similarity	NPD1164	Approved
0.7059	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7874	Approved
0.7048	Intermediate Similarity	NPD37	Approved
0.7037	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7701	Phase 2
0.7033	Intermediate Similarity	NPD6534	Approved
0.7033	Intermediate Similarity	NPD6535	Approved
0.7027	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD422	Phase 1
0.7006	Intermediate Similarity	NPD8312	Approved
0.7006	Intermediate Similarity	NPD8313	Approved
0.6983	Remote Similarity	NPD8434	Phase 2
0.698	Remote Similarity	NPD9269	Phase 2
0.698	Remote Similarity	NPD1608	Approved
0.6971	Remote Similarity	NPD1729	Discontinued
0.6968	Remote Similarity	NPD4060	Phase 1
0.6964	Remote Similarity	NPD4288	Approved
0.6948	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6234	Discontinued
0.6939	Remote Similarity	NPD5691	Approved
0.6939	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9268	Approved
0.6927	Remote Similarity	NPD7801	Approved
0.6923	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD4965	Approved
0.6923	Remote Similarity	NPD4967	Phase 2
0.6919	Remote Similarity	NPD7229	Phase 3
0.6919	Remote Similarity	NPD7700	Phase 2
0.6919	Remote Similarity	NPD3787	Discontinued
0.6919	Remote Similarity	NPD7699	Phase 2
0.6914	Remote Similarity	NPD3300	Phase 2
0.6913	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1610	Phase 2
0.6899	Remote Similarity	NPD4308	Phase 3
0.6893	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8320	Phase 1
0.6878	Remote Similarity	NPD8319	Approved
0.6875	Remote Similarity	NPD1241	Discontinued
0.6865	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2296	Approved
0.6857	Remote Similarity	NPD7177	Discontinued
0.6857	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4750	Phase 3
0.6829	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4908	Phase 1
0.6818	Remote Similarity	NPD6832	Phase 2
0.6815	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4287	Approved
0.6792	Remote Similarity	NPD3299	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