NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.07
Volume:	235.634
LogP:	1.865
LogD:	1.775
LogS:	-4.02
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.782
Synthetic Accessibility Score:	2.213
Fsp3:	0.231
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:	-4.649
MDCK Permeability:	2.606876842037309e-05
Pgp-inhibitor:	0.124
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.263
Plasma Protein Binding (PPB):	85.01268768310547%
Volume Distribution (VD):	0.806
Pgp-substrate:	8.225735664367676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.767
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.598
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.695
CYP2D6-substrate:	0.704
CYP3A4-inhibitor:	0.697
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	9.287
Half-life (T1/2):	0.366

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.695
AMES Toxicity:	0.801
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.648
Skin Sensitization:	0.857
Carcinogencity:	0.846
Eye Corrosion:	0.197
Eye Irritation:	0.987
Respiratory Toxicity:	0.841

Download Data

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

Natural Product: NPC45537

Natural Product ID:	NPC45537
*Common Name:**	5,8-Dimethoxy-2-Methylnaphthalene-1,4-Dione
IUPAC Name:	5,8-dimethoxy-2-methylnaphthalene-1,4-dione
Synonyms:
Standard InCHIKey:	LQTITSAGIIHACG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H12O4/c1-7-6-8(14)11-9(16-2)4-5-10(17-3)12(11)13(7)15/h4-6H,1-3H3
SMILES:	CC1=CC(=O)c2c(ccc(c2C1=O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071231
PubChem CID:	13142440
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[565111]

☑ 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 NPC45537 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	402
0.1-0.2	1781
0.2-0.3	4859
0.3-0.4	11602
0.4-0.5	6192
0.5-0.6	5251
0.6-0.7	8693
0.7-0.8	3728
0.8-0.85	150
0.85-0.9	32
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC182646
0.9375	High Similarity	NPC281513
0.9375	High Similarity	NPC22222
0.9365	High Similarity	NPC205360
0.9008	High Similarity	NPC232996
0.8939	High Similarity	NPC301341
0.8939	High Similarity	NPC284184
0.8915	High Similarity	NPC477412
0.8906	High Similarity	NPC57552
0.8889	High Similarity	NPC224657
0.8855	High Similarity	NPC1249
0.8852	High Similarity	NPC171023
0.8815	High Similarity	NPC124365
0.8806	High Similarity	NPC477408
0.8759	High Similarity	NPC89664
0.8759	High Similarity	NPC274085
0.875	High Similarity	NPC298884
0.875	High Similarity	NPC470841
0.8722	High Similarity	NPC141934
0.8702	High Similarity	NPC474340
0.8682	High Similarity	NPC237225
0.8672	High Similarity	NPC306765
0.8661	High Similarity	NPC56332
0.8657	High Similarity	NPC471542
0.8623	High Similarity	NPC477409
0.8561	High Similarity	NPC472882
0.856	High Similarity	NPC206778
0.856	High Similarity	NPC285829
0.854	High Similarity	NPC149780
0.854	High Similarity	NPC84273
0.8529	High Similarity	NPC1268
0.8529	High Similarity	NPC223336
0.8527	High Similarity	NPC177925
0.8527	High Similarity	NPC51037
0.8516	High Similarity	NPC4012
0.8516	High Similarity	NPC310540
0.85	High Similarity	NPC300540
0.848	Intermediate Similarity	NPC232178
0.8467	Intermediate Similarity	NPC109007
0.8462	Intermediate Similarity	NPC71525
0.8443	Intermediate Similarity	NPC279916
0.8421	Intermediate Similarity	NPC246693
0.8421	Intermediate Similarity	NPC110609
0.8421	Intermediate Similarity	NPC477406
0.8421	Intermediate Similarity	NPC242358
0.8409	Intermediate Similarity	NPC198305
0.8394	Intermediate Similarity	NPC216312
0.8394	Intermediate Similarity	NPC471602
0.8394	Intermediate Similarity	NPC476477
0.8394	Intermediate Similarity	NPC29771
0.8394	Intermediate Similarity	NPC299405
0.8394	Intermediate Similarity	NPC111422
0.8394	Intermediate Similarity	NPC306835
0.8394	Intermediate Similarity	NPC256463
0.8385	Intermediate Similarity	NPC474264
0.8385	Intermediate Similarity	NPC96915
0.8385	Intermediate Similarity	NPC474737
0.8385	Intermediate Similarity	NPC1991
0.8372	Intermediate Similarity	NPC470163
0.8372	Intermediate Similarity	NPC470162
0.8359	Intermediate Similarity	NPC307174
0.8357	Intermediate Similarity	NPC475201
0.8346	Intermediate Similarity	NPC141549
0.8345	Intermediate Similarity	NPC329493
0.8345	Intermediate Similarity	NPC69755
0.8333	Intermediate Similarity	NPC220496
0.8333	Intermediate Similarity	NPC42262
0.8333	Intermediate Similarity	NPC201284
0.8333	Intermediate Similarity	NPC37992
0.8333	Intermediate Similarity	NPC241349
0.8333	Intermediate Similarity	NPC32749
0.8333	Intermediate Similarity	NPC327916
0.8333	Intermediate Similarity	NPC147542
0.8293	Intermediate Similarity	NPC53953
0.8286	Intermediate Similarity	NPC277369
0.8286	Intermediate Similarity	NPC215451
0.8286	Intermediate Similarity	NPC476473
0.8286	Intermediate Similarity	NPC53016
0.8284	Intermediate Similarity	NPC183103
0.8284	Intermediate Similarity	NPC118253
0.8273	Intermediate Similarity	NPC471444
0.8273	Intermediate Similarity	NPC257003
0.8271	Intermediate Similarity	NPC7569
0.8271	Intermediate Similarity	NPC278787
0.8261	Intermediate Similarity	NPC470407
0.8258	Intermediate Similarity	NPC165257
0.8252	Intermediate Similarity	NPC474107
0.8244	Intermediate Similarity	NPC3224
0.8244	Intermediate Similarity	NPC231774
0.824	Intermediate Similarity	NPC108288
0.8235	Intermediate Similarity	NPC217914
0.8222	Intermediate Similarity	NPC171968
0.8222	Intermediate Similarity	NPC470406
0.8214	Intermediate Similarity	NPC474300
0.8209	Intermediate Similarity	NPC205992
0.8209	Intermediate Similarity	NPC279596
0.8209	Intermediate Similarity	NPC239134
0.8195	Intermediate Similarity	NPC278928
0.8182	Intermediate Similarity	NPC471530
0.8175	Intermediate Similarity	NPC472881
0.8169	Intermediate Similarity	NPC73416
0.8169	Intermediate Similarity	NPC478019
0.8169	Intermediate Similarity	NPC160777
0.8169	Intermediate Similarity	NPC49282
0.8163	Intermediate Similarity	NPC3898
0.816	Intermediate Similarity	NPC188907
0.816	Intermediate Similarity	NPC240163
0.8156	Intermediate Similarity	NPC167663
0.8154	Intermediate Similarity	NPC375356
0.8148	Intermediate Similarity	NPC309430
0.8138	Intermediate Similarity	NPC294646
0.8134	Intermediate Similarity	NPC475741
0.8134	Intermediate Similarity	NPC473271
0.813	Intermediate Similarity	NPC54626
0.8125	Intermediate Similarity	NPC5537
0.8125	Intermediate Similarity	NPC470092
0.811	Intermediate Similarity	NPC32298
0.8102	Intermediate Similarity	NPC22644
0.8099	Intermediate Similarity	NPC19896
0.8099	Intermediate Similarity	NPC229787
0.8092	Intermediate Similarity	NPC234890
0.8092	Intermediate Similarity	NPC30216
0.8092	Intermediate Similarity	NPC74507
0.8077	Intermediate Similarity	NPC46634
0.8077	Intermediate Similarity	NPC300274
0.8077	Intermediate Similarity	NPC217756
0.8074	Intermediate Similarity	NPC301717
0.8074	Intermediate Similarity	NPC164295
0.806	Intermediate Similarity	NPC34414
0.806	Intermediate Similarity	NPC146647
0.8058	Intermediate Similarity	NPC61590
0.8058	Intermediate Similarity	NPC475104
0.8058	Intermediate Similarity	NPC98395
0.8058	Intermediate Similarity	NPC265181
0.8058	Intermediate Similarity	NPC173980
0.8056	Intermediate Similarity	NPC252208
0.8056	Intermediate Similarity	NPC478018
0.8054	Intermediate Similarity	NPC67197
0.8047	Intermediate Similarity	NPC35744
0.8047	Intermediate Similarity	NPC54243
0.8045	Intermediate Similarity	NPC428300
0.8042	Intermediate Similarity	NPC473951
0.8042	Intermediate Similarity	NPC28632
0.8031	Intermediate Similarity	NPC240664
0.8031	Intermediate Similarity	NPC217423
0.8031	Intermediate Similarity	NPC269414
0.803	Intermediate Similarity	NPC103540
0.8029	Intermediate Similarity	NPC274876
0.8015	Intermediate Similarity	NPC470160
0.8015	Intermediate Similarity	NPC88864
0.8015	Intermediate Similarity	NPC135062
0.8015	Intermediate Similarity	NPC251549
0.8014	Intermediate Similarity	NPC145673
0.8014	Intermediate Similarity	NPC216917
0.8014	Intermediate Similarity	NPC283292
0.8	Intermediate Similarity	NPC199253
0.8	Intermediate Similarity	NPC314329
0.8	Intermediate Similarity	NPC295339
0.8	Intermediate Similarity	NPC476191
0.8	Intermediate Similarity	NPC216624
0.8	Intermediate Similarity	NPC55949
0.8	Intermediate Similarity	NPC136588
0.8	Intermediate Similarity	NPC117609
0.7986	Intermediate Similarity	NPC477534
0.7986	Intermediate Similarity	NPC60389
0.7986	Intermediate Similarity	NPC186647
0.7986	Intermediate Similarity	NPC211565
0.7986	Intermediate Similarity	NPC305060
0.7985	Intermediate Similarity	NPC282923
0.7984	Intermediate Similarity	NPC7151
0.7984	Intermediate Similarity	NPC23332
0.7984	Intermediate Similarity	NPC473662
0.7984	Intermediate Similarity	NPC230951
0.7984	Intermediate Similarity	NPC216297
0.7971	Intermediate Similarity	NPC95485
0.7971	Intermediate Similarity	NPC88065
0.7971	Intermediate Similarity	NPC470844
0.7971	Intermediate Similarity	NPC298900
0.7971	Intermediate Similarity	NPC143649
0.7971	Intermediate Similarity	NPC89504
0.797	Intermediate Similarity	NPC227741
0.797	Intermediate Similarity	NPC49647
0.797	Intermediate Similarity	NPC237868
0.797	Intermediate Similarity	NPC295202
0.797	Intermediate Similarity	NPC136342
0.7969	Intermediate Similarity	NPC166591
0.7959	Intermediate Similarity	NPC144283
0.7958	Intermediate Similarity	NPC11314
0.7958	Intermediate Similarity	NPC49108
0.7956	Intermediate Similarity	NPC59459
0.7956	Intermediate Similarity	NPC254603
0.7956	Intermediate Similarity	NPC193169
0.7956	Intermediate Similarity	NPC477536
0.7955	Intermediate Similarity	NPC68756
0.7955	Intermediate Similarity	NPC142956
0.7955	Intermediate Similarity	NPC75432
0.7955	Intermediate Similarity	NPC152525
0.7955	Intermediate Similarity	NPC91475
0.7955	Intermediate Similarity	NPC265910
0.7945	Intermediate Similarity	NPC70764

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 NPC45537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	983
0.2-0.3	1495
0.3-0.4	2677
0.4-0.5	1913
0.5-0.6	1133
0.6-0.7	479
0.7-0.8	88
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8321	Intermediate Similarity	NPD2346	Discontinued
0.824	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD2935	Discontinued
0.8058	Intermediate Similarity	NPD1471	Phase 3
0.803	Intermediate Similarity	NPD1470	Approved
0.8	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD2798	Approved
0.7955	Intermediate Similarity	NPD1876	Approved
0.7945	Intermediate Similarity	NPD3226	Approved
0.7907	Intermediate Similarity	NPD1651	Approved
0.7868	Intermediate Similarity	NPD2313	Discontinued
0.7857	Intermediate Similarity	NPD1241	Discontinued
0.7826	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD2799	Discontinued
0.7727	Intermediate Similarity	NPD1281	Approved
0.7727	Intermediate Similarity	NPD1201	Approved
0.7721	Intermediate Similarity	NPD6832	Phase 2
0.7704	Intermediate Similarity	NPD1019	Discontinued
0.7698	Intermediate Similarity	NPD447	Suspended
0.7669	Intermediate Similarity	NPD3972	Approved
0.7669	Intermediate Similarity	NPD9717	Approved
0.7622	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD411	Approved
0.7594	Intermediate Similarity	NPD1611	Approved
0.7561	Intermediate Similarity	NPD164	Approved
0.7559	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1283	Approved
0.7552	Intermediate Similarity	NPD2344	Approved
0.7538	Intermediate Similarity	NPD9493	Approved
0.7518	Intermediate Similarity	NPD1607	Approved
0.7517	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD5691	Approved
0.7444	Intermediate Similarity	NPD4626	Approved
0.7434	Intermediate Similarity	NPD6844	Discontinued
0.7431	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1510	Phase 2
0.7413	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3748	Approved
0.7386	Intermediate Similarity	NPD7819	Suspended
0.7376	Intermediate Similarity	NPD2979	Phase 3
0.7372	Intermediate Similarity	NPD5494	Approved
0.7361	Intermediate Similarity	NPD2796	Approved
0.7347	Intermediate Similarity	NPD2309	Approved
0.7324	Intermediate Similarity	NPD1933	Approved
0.7323	Intermediate Similarity	NPD2182	Approved
0.7315	Intermediate Similarity	NPD2533	Approved
0.7315	Intermediate Similarity	NPD2534	Approved
0.7315	Intermediate Similarity	NPD2532	Approved
0.7279	Intermediate Similarity	NPD7003	Approved
0.7278	Intermediate Similarity	NPD6232	Discontinued
0.7273	Intermediate Similarity	NPD2801	Approved
0.7259	Intermediate Similarity	NPD3496	Discontinued
0.7254	Intermediate Similarity	NPD4307	Phase 2
0.725	Intermediate Similarity	NPD7473	Discontinued
0.7241	Intermediate Similarity	NPD1551	Phase 2
0.7226	Intermediate Similarity	NPD5402	Approved
0.7219	Intermediate Similarity	NPD920	Approved
0.7218	Intermediate Similarity	NPD5536	Phase 2
0.7215	Intermediate Similarity	NPD1247	Approved
0.72	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9261	Approved
0.7185	Intermediate Similarity	NPD17	Approved
0.7185	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7133	Intermediate Similarity	NPD1511	Approved
0.7124	Intermediate Similarity	NPD2649	Approved
0.7124	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2651	Approved
0.7122	Intermediate Similarity	NPD3266	Approved
0.7122	Intermediate Similarity	NPD3267	Approved
0.7113	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1243	Approved
0.7095	Intermediate Similarity	NPD2800	Approved
0.7086	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3300	Phase 2
0.7063	Intermediate Similarity	NPD8032	Phase 2
0.7055	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7051	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1512	Approved
0.7039	Intermediate Similarity	NPD6273	Approved
0.7029	Intermediate Similarity	NPD1608	Approved
0.702	Intermediate Similarity	NPD6799	Approved
0.7007	Intermediate Similarity	NPD2438	Suspended
0.7007	Intermediate Similarity	NPD2531	Phase 2
0.7006	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6959	Discontinued
0.6987	Remote Similarity	NPD1934	Approved
0.6987	Remote Similarity	NPD6280	Approved
0.6987	Remote Similarity	NPD6279	Approved
0.6985	Remote Similarity	NPD5585	Approved
0.698	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD9267	Approved
0.6977	Remote Similarity	NPD9263	Approved
0.6977	Remote Similarity	NPD9264	Approved
0.6968	Remote Similarity	NPD6599	Discontinued
0.6968	Remote Similarity	NPD4380	Phase 2
0.6962	Remote Similarity	NPD3882	Suspended
0.6959	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD9697	Approved
0.6947	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.694	Remote Similarity	NPD709	Approved
0.694	Remote Similarity	NPD6671	Approved
0.6934	Remote Similarity	NPD1778	Approved
0.6933	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD74	Approved
0.6923	Remote Similarity	NPD9266	Approved
0.6914	Remote Similarity	NPD3926	Phase 2
0.6906	Remote Similarity	NPD1481	Phase 2
0.6903	Remote Similarity	NPD7458	Discontinued
0.6899	Remote Similarity	NPD3817	Phase 2
0.6897	Remote Similarity	NPD3142	Approved
0.6897	Remote Similarity	NPD3140	Approved
0.6897	Remote Similarity	NPD943	Approved
0.6892	Remote Similarity	NPD5404	Approved
0.6892	Remote Similarity	NPD5406	Approved
0.6892	Remote Similarity	NPD5405	Approved
0.6892	Remote Similarity	NPD5408	Approved
0.6879	Remote Similarity	NPD1164	Approved
0.6879	Remote Similarity	NPD2797	Approved
0.6875	Remote Similarity	NPD7985	Registered
0.6875	Remote Similarity	NPD919	Approved
0.6875	Remote Similarity	NPD3764	Approved
0.6875	Remote Similarity	NPD3268	Approved
0.6867	Remote Similarity	NPD2654	Approved
0.6863	Remote Similarity	NPD5401	Approved
0.6863	Remote Similarity	NPD4662	Approved
0.6863	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4661	Approved
0.6861	Remote Similarity	NPD3024	Approved
0.6861	Remote Similarity	NPD3025	Approved
0.6857	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5844	Phase 1
0.6846	Remote Similarity	NPD1358	Approved
0.6845	Remote Similarity	NPD8312	Approved
0.6845	Remote Similarity	NPD8313	Approved
0.6838	Remote Similarity	NPD7644	Approved
0.6835	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1535	Discovery
0.6821	Remote Similarity	NPD4628	Phase 3
0.6815	Remote Similarity	NPD7411	Suspended
0.6813	Remote Similarity	NPD3749	Approved
0.6812	Remote Similarity	NPD2932	Approved
0.6803	Remote Similarity	NPD6651	Approved
0.6797	Remote Similarity	NPD7390	Discontinued
0.6792	Remote Similarity	NPD2296	Approved
0.6792	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD496	Approved
0.6791	Remote Similarity	NPD5283	Phase 1
0.6791	Remote Similarity	NPD498	Approved
0.6791	Remote Similarity	NPD495	Approved
0.6791	Remote Similarity	NPD1398	Phase 1
0.6788	Remote Similarity	NPD9545	Approved
0.6788	Remote Similarity	NPD3751	Discontinued
0.6788	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4477	Approved
0.6779	Remote Similarity	NPD4476	Approved
0.6774	Remote Similarity	NPD5403	Approved
0.6769	Remote Similarity	NPD3134	Approved
0.6763	Remote Similarity	NPD3023	Approved
0.6763	Remote Similarity	NPD3026	Approved
0.6753	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.675	Remote Similarity	NPD650	Approved
0.675	Remote Similarity	NPD7768	Phase 2
0.6748	Remote Similarity	NPD5710	Approved
0.6748	Remote Similarity	NPD5711	Approved
0.6748	Remote Similarity	NPD6808	Phase 2
0.6741	Remote Similarity	NPD497	Approved
0.6741	Remote Similarity	NPD9281	Approved
0.6738	Remote Similarity	NPD4359	Approved
0.6735	Remote Similarity	NPD4622	Approved
0.6735	Remote Similarity	NPD4618	Approved
0.6732	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5889	Approved
0.6709	Remote Similarity	NPD5890	Approved
0.6708	Remote Similarity	NPD7075	Discontinued
0.6693	Remote Similarity	NPD1238	Approved
0.6691	Remote Similarity	NPD3019	Approved
0.669	Remote Similarity	NPD6696	Suspended
0.6687	Remote Similarity	NPD5978	Approved
0.6687	Remote Similarity	NPD5977	Approved
0.6685	Remote Similarity	NPD6781	Approved
0.6685	Remote Similarity	NPD6780	Approved
0.6685	Remote Similarity	NPD6776	Approved
0.6685	Remote Similarity	NPD6778	Approved
0.6685	Remote Similarity	NPD6779	Approved
0.6685	Remote Similarity	NPD6777	Approved
0.6685	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD6099	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