NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	269.07
Volume:	267.393
LogP:	2.55
LogD:	1.998
LogS:	-4.866
# Rotatable Bonds:	1
TPSA:	76.23
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	2.461
Fsp3:	0.133
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:	-5.002
MDCK Permeability:	1.5833793440833688e-05
Pgp-inhibitor:	0.704
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	94.90186309814453%
Volume Distribution (VD):	0.409
Pgp-substrate:	1.3519665002822876%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.23
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.54
CYP2C9-substrate:	0.25
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.353
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	6.512
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.894
Rat Oral Acute Toxicity:	0.32
Maximum Recommended Daily Dose:	0.277
Skin Sensitization:	0.153
Carcinogencity:	0.667
Eye Corrosion:	0.004
Eye Irritation:	0.726
Respiratory Toxicity:	0.396

Download Data

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

Natural Product: NPC232225

Natural Product ID:	NPC232225
*Common Name:**	Dielsiquinone
IUPAC Name:	3-methoxy-4-methyl-1H-benzo[g]quinoline-2,5,10-trione
Synonyms:	Dielsiquinone
Standard InCHIKey:	AZTABGJRYQJTCL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H11NO4/c1-7-10-11(16-15(19)14(7)20-2)13(18)9-6-4-3-5-8(9)12(10)17/h3-6H,1-2H3,(H,16,19)
SMILES:	COc1c(O)nc2c(c1C)C(=O)c1c(C2=O)cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479282
PubChem CID:	10445779
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines

*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
NPO27762	Goniothalamus marcanii	Species	Annonaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[10543899]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1222	Baccharis scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1843	Laurelia sempervirens	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6982	Cheimophila salicella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13861	Niphates rowi	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3090	Verbascum undulatum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27762	Goniothalamus marcanii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	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
ED50	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.11	uM	PMID[506331]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.12	uM	PMID[506331]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	0.11	uM	PMID[506331]
NPT380	Cell Line	U-251	Homo sapiens	ED50	=	0.37	uM	PMID[506331]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.11	uM	PMID[506331]

☑ 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 NPC232225 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	405
0.1-0.2	2542
0.2-0.3	10036
0.3-0.4	6711
0.4-0.5	11754
0.5-0.6	9853
0.6-0.7	1187
0.7-0.8	199
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC94842
0.8706	High Similarity	NPC220337
0.8394	Intermediate Similarity	NPC206186
0.7753	Intermediate Similarity	NPC15406
0.7751	Intermediate Similarity	NPC304183
0.7665	Intermediate Similarity	NPC67659
0.765	Intermediate Similarity	NPC288987
0.7628	Intermediate Similarity	NPC146976
0.7626	Intermediate Similarity	NPC210434
0.7626	Intermediate Similarity	NPC216612
0.7581	Intermediate Similarity	NPC236668
0.7578	Intermediate Similarity	NPC24019
0.7544	Intermediate Similarity	NPC41501
0.7532	Intermediate Similarity	NPC478045
0.7511	Intermediate Similarity	NPC210296
0.7511	Intermediate Similarity	NPC475844
0.7479	Intermediate Similarity	NPC77878
0.7478	Intermediate Similarity	NPC22481
0.7476	Intermediate Similarity	NPC230403
0.7455	Intermediate Similarity	NPC246381
0.7434	Intermediate Similarity	NPC233334
0.7406	Intermediate Similarity	NPC317572
0.7404	Intermediate Similarity	NPC183537
0.7386	Intermediate Similarity	NPC132385
0.7381	Intermediate Similarity	NPC280714
0.738	Intermediate Similarity	NPC189903
0.738	Intermediate Similarity	NPC182907
0.7368	Intermediate Similarity	NPC90875
0.7364	Intermediate Similarity	NPC184408
0.7345	Intermediate Similarity	NPC278525
0.7339	Intermediate Similarity	NPC208522
0.7336	Intermediate Similarity	NPC108342
0.7319	Intermediate Similarity	NPC270515
0.7313	Intermediate Similarity	NPC472168
0.731	Intermediate Similarity	NPC470894
0.7301	Intermediate Similarity	NPC274640
0.7293	Intermediate Similarity	NPC208898
0.7268	Intermediate Similarity	NPC194040
0.7257	Intermediate Similarity	NPC74575
0.7256	Intermediate Similarity	NPC472286
0.7256	Intermediate Similarity	NPC472287
0.7248	Intermediate Similarity	NPC187501
0.7246	Intermediate Similarity	NPC9729
0.7237	Intermediate Similarity	NPC474701
0.7237	Intermediate Similarity	NPC474688
0.7234	Intermediate Similarity	NPC107123
0.7227	Intermediate Similarity	NPC298449
0.7222	Intermediate Similarity	NPC321428
0.722	Intermediate Similarity	NPC225279
0.7215	Intermediate Similarity	NPC51854
0.7215	Intermediate Similarity	NPC165964
0.7212	Intermediate Similarity	NPC470018
0.7205	Intermediate Similarity	NPC49547
0.7202	Intermediate Similarity	NPC470020
0.7198	Intermediate Similarity	NPC166722
0.7191	Intermediate Similarity	NPC124313
0.7182	Intermediate Similarity	NPC39500
0.7179	Intermediate Similarity	NPC207283
0.7179	Intermediate Similarity	NPC84164
0.7174	Intermediate Similarity	NPC329631
0.7168	Intermediate Similarity	NPC179287
0.7162	Intermediate Similarity	NPC246658
0.716	Intermediate Similarity	NPC215837
0.7156	Intermediate Similarity	NPC144452
0.7149	Intermediate Similarity	NPC160100
0.7149	Intermediate Similarity	NPC118228
0.7149	Intermediate Similarity	NPC129897
0.7131	Intermediate Similarity	NPC209981
0.713	Intermediate Similarity	NPC174576
0.7129	Intermediate Similarity	NPC194724
0.7124	Intermediate Similarity	NPC51388
0.7124	Intermediate Similarity	NPC314633
0.7124	Intermediate Similarity	NPC322482
0.7124	Intermediate Similarity	NPC205372
0.7119	Intermediate Similarity	NPC185197
0.7115	Intermediate Similarity	NPC44354
0.7113	Intermediate Similarity	NPC302807
0.7082	Intermediate Similarity	NPC470022
0.7081	Intermediate Similarity	NPC144381
0.7071	Intermediate Similarity	NPC134637
0.7061	Intermediate Similarity	NPC200888
0.7059	Intermediate Similarity	NPC474428
0.7045	Intermediate Similarity	NPC124086
0.7042	Intermediate Similarity	NPC473188
0.7042	Intermediate Similarity	NPC67401
0.7039	Intermediate Similarity	NPC470017
0.7035	Intermediate Similarity	NPC121069
0.7034	Intermediate Similarity	NPC72905
0.7031	Intermediate Similarity	NPC478078
0.7022	Intermediate Similarity	NPC208084
0.7014	Intermediate Similarity	NPC146418
0.7014	Intermediate Similarity	NPC87413
0.7009	Intermediate Similarity	NPC293151
0.7004	Intermediate Similarity	NPC316224
0.7004	Intermediate Similarity	NPC142385
0.6995	Remote Similarity	NPC303225
0.6992	Remote Similarity	NPC49672
0.6992	Remote Similarity	NPC148889
0.6987	Remote Similarity	NPC218388
0.6987	Remote Similarity	NPC285254
0.6986	Remote Similarity	NPC283117
0.6986	Remote Similarity	NPC193238
0.6982	Remote Similarity	NPC38237
0.6978	Remote Similarity	NPC131885
0.6971	Remote Similarity	NPC42591
0.6967	Remote Similarity	NPC258048
0.696	Remote Similarity	NPC473639
0.6959	Remote Similarity	NPC66815
0.6952	Remote Similarity	NPC183805
0.6951	Remote Similarity	NPC324361
0.6951	Remote Similarity	NPC282346
0.6951	Remote Similarity	NPC89508
0.6947	Remote Similarity	NPC148409
0.6946	Remote Similarity	NPC191310
0.6941	Remote Similarity	NPC45190
0.6941	Remote Similarity	NPC300156
0.6937	Remote Similarity	NPC294375
0.6933	Remote Similarity	NPC291609
0.693	Remote Similarity	NPC472284
0.6923	Remote Similarity	NPC320394
0.6923	Remote Similarity	NPC253675
0.692	Remote Similarity	NPC239763
0.692	Remote Similarity	NPC2905
0.692	Remote Similarity	NPC119134
0.692	Remote Similarity	NPC190401
0.6916	Remote Similarity	NPC469439
0.6916	Remote Similarity	NPC109922
0.6909	Remote Similarity	NPC222561
0.6909	Remote Similarity	NPC308943
0.6909	Remote Similarity	NPC474595
0.6903	Remote Similarity	NPC247803
0.6901	Remote Similarity	NPC137353
0.6895	Remote Similarity	NPC132539
0.6891	Remote Similarity	NPC124300
0.6887	Remote Similarity	NPC114974
0.6886	Remote Similarity	NPC7560
0.688	Remote Similarity	NPC172222
0.6878	Remote Similarity	NPC39679
0.6878	Remote Similarity	NPC90185
0.6875	Remote Similarity	NPC58209
0.6875	Remote Similarity	NPC114468
0.6858	Remote Similarity	NPC268393
0.6858	Remote Similarity	NPC191088
0.6858	Remote Similarity	NPC13599
0.6858	Remote Similarity	NPC303384
0.6858	Remote Similarity	NPC3214
0.6858	Remote Similarity	NPC298840
0.6858	Remote Similarity	NPC312645
0.6852	Remote Similarity	NPC17677
0.6851	Remote Similarity	NPC182222
0.6851	Remote Similarity	NPC34770
0.6846	Remote Similarity	NPC161801
0.6842	Remote Similarity	NPC150239
0.6842	Remote Similarity	NPC174760
0.684	Remote Similarity	NPC469489
0.684	Remote Similarity	NPC227824
0.6833	Remote Similarity	NPC314297
0.6833	Remote Similarity	NPC315545
0.6833	Remote Similarity	NPC249583
0.6833	Remote Similarity	NPC4687
0.6828	Remote Similarity	NPC204446
0.6828	Remote Similarity	NPC134702
0.6828	Remote Similarity	NPC182853
0.6825	Remote Similarity	NPC101312
0.6822	Remote Similarity	NPC45850
0.6812	Remote Similarity	NPC76478
0.6812	Remote Similarity	NPC280799
0.6812	Remote Similarity	NPC164340
0.6812	Remote Similarity	NPC118189
0.681	Remote Similarity	NPC241025
0.681	Remote Similarity	NPC140296
0.6805	Remote Similarity	NPC310618
0.6802	Remote Similarity	NPC100573
0.6802	Remote Similarity	NPC207873
0.68	Remote Similarity	NPC322644
0.68	Remote Similarity	NPC474594
0.6798	Remote Similarity	NPC70949
0.6797	Remote Similarity	NPC473449
0.6796	Remote Similarity	NPC84347
0.6795	Remote Similarity	NPC289905
0.6795	Remote Similarity	NPC316065
0.6793	Remote Similarity	NPC6786
0.6791	Remote Similarity	NPC135950
0.6789	Remote Similarity	NPC318068
0.6787	Remote Similarity	NPC313796
0.6787	Remote Similarity	NPC230683
0.6787	Remote Similarity	NPC313345
0.6787	Remote Similarity	NPC315638
0.6787	Remote Similarity	NPC314855
0.6786	Remote Similarity	NPC295479
0.6786	Remote Similarity	NPC9894
0.6786	Remote Similarity	NPC220241
0.6784	Remote Similarity	NPC116573
0.6783	Remote Similarity	NPC122463
0.678	Remote Similarity	NPC39370
0.6776	Remote Similarity	NPC280964
0.6776	Remote Similarity	NPC114335
0.6776	Remote Similarity	NPC141915
0.6776	Remote Similarity	NPC56170
0.6774	Remote Similarity	NPC89549

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 NPC232225 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	679
0.2-0.3	900
0.3-0.4	1599
0.4-0.5	3066
0.5-0.6	2183
0.6-0.7	417
0.7-0.8	22
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7717	Intermediate Similarity	NPD3925	Approved
0.7431	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5866	Approved
0.7277	Intermediate Similarity	NPD2779	Approved
0.7269	Intermediate Similarity	NPD5022	Discontinued
0.7248	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4429	Discontinued
0.7207	Intermediate Similarity	NPD7395	Discontinued
0.7174	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5416	Discontinued
0.7149	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2778	Approved
0.7106	Intermediate Similarity	NPD6716	Phase 1
0.7106	Intermediate Similarity	NPD1483	Discontinued
0.7064	Intermediate Similarity	NPD5429	Discontinued
0.7061	Intermediate Similarity	NPD3263	Phase 3
0.7027	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5443	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5512	Phase 3
0.6983	Remote Similarity	NPD7031	Phase 1
0.6976	Remote Similarity	NPD3920	Phase 2
0.6955	Remote Similarity	NPD6376	Discontinued
0.6953	Remote Similarity	NPD4373	Phase 2
0.6947	Remote Similarity	NPD6974	Phase 3
0.694	Remote Similarity	NPD6962	Phase 2
0.694	Remote Similarity	NPD1867	Approved
0.6923	Remote Similarity	NPD2951	Discontinued
0.692	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8091	Phase 3
0.6897	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7853	Phase 2
0.6892	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1505	Phase 2
0.6864	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD1638	Discovery
0.6842	Remote Similarity	NPD7180	Phase 3
0.6824	Remote Similarity	NPD4952	Phase 3
0.6824	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3392	Approved
0.681	Remote Similarity	NPD3259	Approved
0.6805	Remote Similarity	NPD5488	Discontinued
0.6798	Remote Similarity	NPD2899	Discontinued
0.6795	Remote Similarity	NPD1466	Phase 3
0.6795	Remote Similarity	NPD1467	Approved
0.6793	Remote Similarity	NPD4368	Phase 2
0.6787	Remote Similarity	NPD3507	Phase 2
0.6786	Remote Similarity	NPD4502	Phase 2
0.6769	Remote Similarity	NPD5850	Phase 3
0.6767	Remote Similarity	NPD5640	Discontinued
0.6762	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD1926	Approved
0.6726	Remote Similarity	NPD3945	Discontinued
0.6725	Remote Similarity	NPD3258	Approved
0.6723	Remote Similarity	NPD5805	Approved
0.6713	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6790	Phase 1
0.6698	Remote Similarity	NPD3924	Approved
0.6698	Remote Similarity	NPD3921	Approved
0.6698	Remote Similarity	NPD3923	Approved
0.6698	Remote Similarity	NPD3922	Approved
0.6695	Remote Similarity	NPD3746	Discontinued
0.6681	Remote Similarity	NPD3006	Discontinued
0.6667	Remote Similarity	NPD4328	Approved
0.6667	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3257	Approved
0.662	Remote Similarity	NPD5256	Discontinued
0.6611	Remote Similarity	NPD3250	Phase 1
0.6585	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8463	Approved
0.6568	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6590	Discontinued
0.6558	Remote Similarity	NPD2792	Approved
0.6552	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.654	Remote Similarity	NPD5924	Discontinued
0.654	Remote Similarity	NPD5479	Discontinued
0.6532	Remote Similarity	NPD5857	Phase 3
0.6525	Remote Similarity	NPD7994	Phase 2
0.6524	Remote Similarity	NPD6159	Phase 2
0.6524	Remote Similarity	NPD7556	Discontinued
0.6522	Remote Similarity	NPD8149	Discontinued
0.652	Remote Similarity	NPD1685	Approved
0.652	Remote Similarity	NPD1684	Approved
0.6518	Remote Similarity	NPD5482	Discontinued
0.6518	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD3243	Approved
0.6504	Remote Similarity	NPD3328	Phase 2
0.6502	Remote Similarity	NPD7417	Discontinued
0.6493	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7924	Phase 2
0.6484	Remote Similarity	NPD7925	Phase 2
0.6481	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD2821	Approved
0.6471	Remote Similarity	NPD1659	Phase 1
0.6471	Remote Similarity	NPD772	Phase 3
0.6468	Remote Similarity	NPD7279	Phase 2
0.6468	Remote Similarity	NPD7278	Phase 2
0.6466	Remote Similarity	NPD5632	Approved
0.6463	Remote Similarity	NPD7069	Discontinued
0.6463	Remote Similarity	NPD4927	Discontinued
0.6462	Remote Similarity	NPD9510	Approved
0.6462	Remote Similarity	NPD1643	Phase 3
0.6461	Remote Similarity	NPD7886	Phase 2
0.6461	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7885	Phase 2
0.646	Remote Similarity	NPD7222	Phase 2
0.6458	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6550	Discontinued
0.6453	Remote Similarity	NPD4923	Phase 1
0.6452	Remote Similarity	NPD2564	Approved
0.6452	Remote Similarity	NPD2565	Phase 2
0.6449	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD1225	Phase 2
0.6448	Remote Similarity	NPD1224	Phase 2
0.6447	Remote Similarity	NPD5860	Discontinued
0.6447	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5914	Approved
0.6445	Remote Similarity	NPD6642	Approved
0.6445	Remote Similarity	NPD6641	Approved
0.6443	Remote Similarity	NPD6530	Approved
0.6443	Remote Similarity	NPD7708	Approved
0.6443	Remote Similarity	NPD6531	Approved
0.644	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4204	Approved
0.6432	Remote Similarity	NPD2916	Discontinued
0.6432	Remote Similarity	NPD4203	Approved
0.6432	Remote Similarity	NPD7467	Discontinued
0.6431	Remote Similarity	NPD6456	Discontinued
0.6426	Remote Similarity	NPD6209	Approved
0.6426	Remote Similarity	NPD8356	Approved
0.6422	Remote Similarity	NPD4989	Phase 2
0.642	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4885	Approved
0.6416	Remote Similarity	NPD5530	Phase 1
0.6408	Remote Similarity	NPD7022	Phase 2
0.6408	Remote Similarity	NPD1631	Approved
0.6404	Remote Similarity	NPD4506	Discontinued
0.64	Remote Similarity	NPD2920	Discontinued
0.6397	Remote Similarity	NPD5817	Discontinued
0.6395	Remote Similarity	NPD6568	Discontinued
0.6391	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD8430	Approved
0.6387	Remote Similarity	NPD4845	Discontinued
0.6385	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.638	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3298	Approved
0.6368	Remote Similarity	NPD2176	Approved
0.6368	Remote Similarity	NPD2177	Approved
0.6368	Remote Similarity	NPD6770	Approved
0.6368	Remote Similarity	NPD2175	Phase 3
0.6364	Remote Similarity	NPD3074	Discontinued
0.6359	Remote Similarity	NPD9363	Approved
0.6359	Remote Similarity	NPD9364	Phase 2
0.6356	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6988	Phase 1
0.6351	Remote Similarity	NPD1229	Phase 2
0.6351	Remote Similarity	NPD5003	Discontinued
0.6348	Remote Similarity	NPD5939	Approved
0.6348	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD683	Approved
0.6348	Remote Similarity	NPD1945	Phase 1
0.6348	Remote Similarity	NPD5936	Approved
0.6342	Remote Similarity	NPD7803	Approved
0.634	Remote Similarity	NPD6242	Discontinued
0.6336	Remote Similarity	NPD5293	Phase 2
0.6335	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD8016	Phase 3
0.6323	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7922	Phase 1
0.632	Remote Similarity	NPD7225	Discontinued
0.632	Remote Similarity	NPD3986	Discontinued
0.6318	Remote Similarity	NPD6569	Phase 2
0.6316	Remote Similarity	NPD7453	Approved
0.6316	Remote Similarity	NPD7452	Approved
0.6316	Remote Similarity	NPD6290	Phase 2
0.6311	Remote Similarity	NPD946	Discontinued
0.6311	Remote Similarity	NPD6321	Discontinued
0.631	Remote Similarity	NPD5532	Phase 2

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