NPASS Compound

Structure

NPC134702 OpenBabel07101719142D 21 23 0 0 0 0 0 0 0 0999 V2000 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 9 2 0 0 0 0 7 10 2 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 19 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	285.1
Volume:	287.325
LogP:	2.262
LogD:	2.376
LogS:	-3.826
# Rotatable Bonds:	2
TPSA:	60.69
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	2.289
Fsp3:	0.188
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:	-4.83
MDCK Permeability:	2.6338489988120273e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.488
Plasma Protein Binding (PPB):	91.59839630126953%
Volume Distribution (VD):	0.761
Pgp-substrate:	7.0894083976745605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.728
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.704
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.602
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.562
CYP3A4-substrate:	0.382

ADMET: Excretion

Clearance (CL):	4.369
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.084
Drug-inuced Liver Injury (DILI):	0.424
AMES Toxicity:	0.813
Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.411
Skin Sensitization:	0.268
Carcinogencity:	0.924
Eye Corrosion:	0.025
Eye Irritation:	0.949
Respiratory Toxicity:	0.836

Download Data

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

Natural Product: NPC134702

Natural Product ID:	NPC134702
*Common Name:**	3-Hydroxy-1,4-Dimethoxy-10-Methyl-9-Acridone
IUPAC Name:	3-hydroxy-1,4-dimethoxy-10-methylacridin-9-one
Synonyms:
Standard InCHIKey:	IUSDGCPJUCVNHX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H15NO4/c1-17-10-7-5-4-6-9(10)15(19)13-12(20-2)8-11(18)16(21-3)14(13)17/h4-8,18H,1-3H3
SMILES:	COc1cc(O)c(c2c1c(=O)c1c(n2C)cccc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095074
PubChem CID:	46887583
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001811] Acridones

*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
NPO15090	Zanthoxylum leprieurii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20413315]
NPO15090	Zanthoxylum leprieurii	Species	Rutaceae	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
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[540129]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	>	100000.0	nM	PMID[540129]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[540129]

☑ 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 NPC134702 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	615
0.1-0.2	3440
0.2-0.3	12014
0.3-0.4	4970
0.4-0.5	8553
0.5-0.6	10322
0.6-0.7	2470
0.7-0.8	254
0.8-0.85	26
0.85-0.9	13
0.9-0.95	12
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC114468
0.9746	High Similarity	NPC118189
0.9742	High Similarity	NPC148391
0.9742	High Similarity	NPC2905
0.9646	High Similarity	NPC76478
0.9594	High Similarity	NPC182853
0.9548	High Similarity	NPC7560
0.9391	High Similarity	NPC268223
0.9388	High Similarity	NPC220241
0.9388	High Similarity	NPC295479
0.9265	High Similarity	NPC285254
0.922	High Similarity	NPC13249
0.9113	High Similarity	NPC118154
0.9113	High Similarity	NPC157983
0.9086	High Similarity	NPC212123
0.9015	High Similarity	NPC195120
0.8922	High Similarity	NPC87560
0.8911	High Similarity	NPC30749
0.8808	High Similarity	NPC114039
0.8808	High Similarity	NPC206109
0.8768	High Similarity	NPC305542
0.867	High Similarity	NPC474366
0.8585	High Similarity	NPC116178
0.8579	High Similarity	NPC170333
0.8544	High Similarity	NPC217903
0.8537	High Similarity	NPC218303
0.8454	Intermediate Similarity	NPC321166
0.8431	Intermediate Similarity	NPC198160
0.8416	Intermediate Similarity	NPC15987
0.8413	Intermediate Similarity	NPC176113
0.8333	Intermediate Similarity	NPC133156
0.829	Intermediate Similarity	NPC298320
0.8283	Intermediate Similarity	NPC1820
0.8263	Intermediate Similarity	NPC329830
0.8218	Intermediate Similarity	NPC234933
0.8146	Intermediate Similarity	NPC288759
0.7981	Intermediate Similarity	NPC313112
0.7981	Intermediate Similarity	NPC301292
0.7913	Intermediate Similarity	NPC241263
0.7739	Intermediate Similarity	NPC98416
0.772	Intermediate Similarity	NPC204867
0.7629	Intermediate Similarity	NPC107123
0.7607	Intermediate Similarity	NPC134637
0.759	Intermediate Similarity	NPC299582
0.7581	Intermediate Similarity	NPC477825
0.7558	Intermediate Similarity	NPC470481
0.7558	Intermediate Similarity	NPC470482
0.7524	Intermediate Similarity	NPC17677
0.7477	Intermediate Similarity	NPC477826
0.7477	Intermediate Similarity	NPC477827
0.7454	Intermediate Similarity	NPC207873
0.7454	Intermediate Similarity	NPC100573
0.7441	Intermediate Similarity	NPC83019
0.7421	Intermediate Similarity	NPC477828
0.7393	Intermediate Similarity	NPC204580
0.7389	Intermediate Similarity	NPC85613
0.7389	Intermediate Similarity	NPC5167
0.7376	Intermediate Similarity	NPC9475
0.7353	Intermediate Similarity	NPC302807
0.7339	Intermediate Similarity	NPC476258
0.7339	Intermediate Similarity	NPC304837
0.7336	Intermediate Similarity	NPC471489
0.7333	Intermediate Similarity	NPC269451
0.7333	Intermediate Similarity	NPC245382
0.7333	Intermediate Similarity	NPC100263
0.7333	Intermediate Similarity	NPC100971
0.7333	Intermediate Similarity	NPC181209
0.7333	Intermediate Similarity	NPC148124
0.7333	Intermediate Similarity	NPC131266
0.7333	Intermediate Similarity	NPC216769
0.7333	Intermediate Similarity	NPC291802
0.7333	Intermediate Similarity	NPC35763
0.7333	Intermediate Similarity	NPC209487
0.7333	Intermediate Similarity	NPC121522
0.733	Intermediate Similarity	NPC298449
0.7327	Intermediate Similarity	NPC16249
0.7319	Intermediate Similarity	NPC160100
0.7313	Intermediate Similarity	NPC73280
0.7311	Intermediate Similarity	NPC203373
0.7308	Intermediate Similarity	NPC119134
0.7306	Intermediate Similarity	NPC183655
0.7306	Intermediate Similarity	NPC287395
0.7304	Intermediate Similarity	NPC476429
0.7296	Intermediate Similarity	NPC271779
0.7296	Intermediate Similarity	NPC206238
0.7296	Intermediate Similarity	NPC88645
0.7296	Intermediate Similarity	NPC167091
0.7296	Intermediate Similarity	NPC124714
0.7296	Intermediate Similarity	NPC292214
0.7295	Intermediate Similarity	NPC262725
0.7295	Intermediate Similarity	NPC209981
0.7294	Intermediate Similarity	NPC90185
0.7289	Intermediate Similarity	NPC99724
0.7282	Intermediate Similarity	NPC45291
0.7282	Intermediate Similarity	NPC19980
0.7277	Intermediate Similarity	NPC113455
0.7273	Intermediate Similarity	NPC208890
0.7273	Intermediate Similarity	NPC99597
0.7273	Intermediate Similarity	NPC210084
0.7268	Intermediate Similarity	NPC327005
0.7268	Intermediate Similarity	NPC102003
0.7268	Intermediate Similarity	NPC92722
0.7259	Intermediate Similarity	NPC2928
0.7259	Intermediate Similarity	NPC39184
0.7254	Intermediate Similarity	NPC282346
0.7251	Intermediate Similarity	NPC254957
0.7249	Intermediate Similarity	NPC315914
0.7248	Intermediate Similarity	NPC308943
0.7246	Intermediate Similarity	NPC15406
0.7245	Intermediate Similarity	NPC101996
0.7245	Intermediate Similarity	NPC180234
0.7245	Intermediate Similarity	NPC161277
0.7245	Intermediate Similarity	NPC120537
0.7245	Intermediate Similarity	NPC39007
0.7245	Intermediate Similarity	NPC199100
0.7235	Intermediate Similarity	NPC163829
0.7235	Intermediate Similarity	NPC268077
0.7231	Intermediate Similarity	NPC156953
0.7231	Intermediate Similarity	NPC10467
0.7227	Intermediate Similarity	NPC25961
0.7225	Intermediate Similarity	NPC94842
0.7222	Intermediate Similarity	NPC2173
0.7222	Intermediate Similarity	NPC235165
0.7222	Intermediate Similarity	NPC328700
0.7222	Intermediate Similarity	NPC472916
0.7222	Intermediate Similarity	NPC119818
0.7222	Intermediate Similarity	NPC255106
0.7222	Intermediate Similarity	NPC202771
0.7216	Intermediate Similarity	NPC15329
0.7216	Intermediate Similarity	NPC131451
0.7208	Intermediate Similarity	NPC250557
0.7205	Intermediate Similarity	NPC248903
0.7203	Intermediate Similarity	NPC477395
0.7202	Intermediate Similarity	NPC158551
0.7198	Intermediate Similarity	NPC185031
0.7196	Intermediate Similarity	NPC71124
0.7194	Intermediate Similarity	NPC171010
0.7194	Intermediate Similarity	NPC149614
0.7194	Intermediate Similarity	NPC251110
0.7194	Intermediate Similarity	NPC262623
0.7194	Intermediate Similarity	NPC117579
0.7193	Intermediate Similarity	NPC19175
0.7189	Intermediate Similarity	NPC41216
0.7186	Intermediate Similarity	NPC48208
0.7186	Intermediate Similarity	NPC472914
0.7186	Intermediate Similarity	NPC262286
0.7186	Intermediate Similarity	NPC475267
0.7186	Intermediate Similarity	NPC162869
0.7186	Intermediate Similarity	NPC474208
0.7186	Intermediate Similarity	NPC472910
0.7186	Intermediate Similarity	NPC472911
0.7186	Intermediate Similarity	NPC96167
0.7186	Intermediate Similarity	NPC156057
0.7186	Intermediate Similarity	NPC222814
0.7186	Intermediate Similarity	NPC245758
0.7186	Intermediate Similarity	NPC36852
0.7186	Intermediate Similarity	NPC78225
0.7186	Intermediate Similarity	NPC474836
0.7186	Intermediate Similarity	NPC472913
0.7185	Intermediate Similarity	NPC120239
0.7181	Intermediate Similarity	NPC251071
0.7179	Intermediate Similarity	NPC40290
0.7179	Intermediate Similarity	NPC139293
0.7179	Intermediate Similarity	NPC195763
0.7179	Intermediate Similarity	NPC142876
0.7179	Intermediate Similarity	NPC264550
0.7179	Intermediate Similarity	NPC333691
0.7179	Intermediate Similarity	NPC69430
0.7179	Intermediate Similarity	NPC264289
0.7179	Intermediate Similarity	NPC200060
0.7177	Intermediate Similarity	NPC18306
0.7172	Intermediate Similarity	NPC20830
0.7172	Intermediate Similarity	NPC130589
0.7172	Intermediate Similarity	NPC256612
0.7172	Intermediate Similarity	NPC93653
0.7172	Intermediate Similarity	NPC134287
0.7171	Intermediate Similarity	NPC474815
0.717	Intermediate Similarity	NPC78284
0.7167	Intermediate Similarity	NPC160113
0.7167	Intermediate Similarity	NPC476220
0.7165	Intermediate Similarity	NPC93034
0.7165	Intermediate Similarity	NPC119660
0.7164	Intermediate Similarity	NPC308992
0.7162	Intermediate Similarity	NPC26928
0.7162	Intermediate Similarity	NPC476436
0.7157	Intermediate Similarity	NPC188203
0.7157	Intermediate Similarity	NPC293183
0.7157	Intermediate Similarity	NPC83508
0.7157	Intermediate Similarity	NPC198826
0.7157	Intermediate Similarity	NPC187498
0.7157	Intermediate Similarity	NPC275836
0.7157	Intermediate Similarity	NPC301323
0.7157	Intermediate Similarity	NPC120163
0.7157	Intermediate Similarity	NPC100887
0.7157	Intermediate Similarity	NPC222830
0.7157	Intermediate Similarity	NPC25270
0.7157	Intermediate Similarity	NPC156222
0.7157	Intermediate Similarity	NPC212678
0.7157	Intermediate Similarity	NPC71334
0.7157	Intermediate Similarity	NPC256283

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 NPC134702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	709
0.2-0.3	1129
0.3-0.4	1879
0.4-0.5	2677
0.5-0.6	1840
0.6-0.7	509
0.7-0.8	50
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9645	High Similarity	NPD2899	Discontinued
0.7577	Intermediate Similarity	NPD6625	Approved
0.756	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1483	Discontinued
0.7403	Intermediate Similarity	NPD4846	Phase 2
0.7311	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD5860	Discontinued
0.729	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5242	Approved
0.7248	Intermediate Similarity	NPD7263	Phase 2
0.7244	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6874	Approved
0.7235	Intermediate Similarity	NPD3298	Approved
0.7222	Intermediate Similarity	NPD5006	Approved
0.7222	Intermediate Similarity	NPD5005	Approved
0.7198	Intermediate Similarity	NPD7922	Phase 1
0.7189	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5102	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD8461	Discontinued
0.7124	Intermediate Similarity	NPD5496	Approved
0.7121	Intermediate Similarity	NPD2801	Approved
0.7117	Intermediate Similarity	NPD683	Approved
0.7083	Intermediate Similarity	NPD3297	Approved
0.7079	Intermediate Similarity	NPD2821	Approved
0.7071	Intermediate Similarity	NPD1934	Approved
0.7059	Intermediate Similarity	NPD4082	Approved
0.704	Intermediate Similarity	NPD1945	Phase 1
0.7037	Intermediate Similarity	NPD4420	Approved
0.7037	Intermediate Similarity	NPD5071	Phase 2
0.7026	Intermediate Similarity	NPD7654	Discontinued
0.7019	Intermediate Similarity	NPD6104	Discontinued
0.6966	Remote Similarity	NPD8067	Phase 3
0.6961	Remote Similarity	NPD5183	Approved
0.6961	Remote Similarity	NPD5186	Approved
0.6955	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7223	Discontinued
0.694	Remote Similarity	NPD7224	Discontinued
0.6923	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7907	Approved
0.691	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD2339	Phase 3
0.6893	Remote Similarity	NPD1220	Phase 1
0.689	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5197	Approved
0.6881	Remote Similarity	NPD5196	Approved
0.6881	Remote Similarity	NPD5194	Approved
0.6875	Remote Similarity	NPD1221	Approved
0.687	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4596	Phase 1
0.6853	Remote Similarity	NPD7279	Phase 2
0.6853	Remote Similarity	NPD7278	Phase 2
0.6847	Remote Similarity	NPD4467	Phase 2
0.6847	Remote Similarity	NPD4465	Phase 2
0.6835	Remote Similarity	NPD4605	Approved
0.6835	Remote Similarity	NPD4604	Approved
0.683	Remote Similarity	NPD2906	Approved
0.683	Remote Similarity	NPD4022	Approved
0.683	Remote Similarity	NPD2907	Approved
0.683	Remote Similarity	NPD3472	Approved
0.6826	Remote Similarity	NPD4111	Phase 1
0.6826	Remote Similarity	NPD4665	Approved
0.6825	Remote Similarity	NPD7803	Approved
0.6822	Remote Similarity	NPD1898	Discontinued
0.6816	Remote Similarity	NPD8367	Approved
0.6806	Remote Similarity	NPD5937	Approved
0.6804	Remote Similarity	NPD4668	Phase 2
0.6798	Remote Similarity	NPD3882	Suspended
0.6794	Remote Similarity	NPD3793	Phase 3
0.6787	Remote Similarity	NPD2494	Approved
0.6787	Remote Similarity	NPD3452	Approved
0.6787	Remote Similarity	NPD3450	Approved
0.6787	Remote Similarity	NPD2493	Approved
0.6786	Remote Similarity	NPD7584	Approved
0.678	Remote Similarity	NPD6199	Discontinued
0.6776	Remote Similarity	NPD4515	Suspended
0.6774	Remote Similarity	NPD8492	Approved
0.677	Remote Similarity	NPD3372	Discontinued
0.6758	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD7701	Phase 2
0.6751	Remote Similarity	NPD1511	Approved
0.6751	Remote Similarity	NPD1505	Phase 2
0.675	Remote Similarity	NPD824	Approved
0.675	Remote Similarity	NPD7048	Phase 3
0.6749	Remote Similarity	NPD5977	Approved
0.6749	Remote Similarity	NPD5353	Approved
0.6749	Remote Similarity	NPD5978	Approved
0.6744	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.674	Remote Similarity	NPD4493	Discontinued
0.6738	Remote Similarity	NPD6997	Phase 2
0.6731	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6166	Phase 2
0.6714	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5582	Discontinued
0.6711	Remote Similarity	NPD4492	Approved
0.6711	Remote Similarity	NPD4494	Approved
0.6711	Remote Similarity	NPD7043	Discontinued
0.671	Remote Similarity	NPD6198	Phase 1
0.6697	Remote Similarity	NPD7125	Discontinued
0.6697	Remote Similarity	NPD5608	Approved
0.6697	Remote Similarity	NPD5609	Approved
0.6696	Remote Similarity	NPD8149	Discontinued
0.6696	Remote Similarity	NPD6644	Discontinued
0.6696	Remote Similarity	NPD4583	Approved
0.6696	Remote Similarity	NPD4582	Approved
0.6695	Remote Similarity	NPD7805	Phase 3
0.6694	Remote Similarity	NPD7885	Phase 2
0.6694	Remote Similarity	NPD7886	Phase 2
0.6683	Remote Similarity	NPD1512	Approved
0.6682	Remote Similarity	NPD8054	Approved
0.6682	Remote Similarity	NPD8053	Approved
0.6681	Remote Similarity	NPD7585	Approved
0.6667	Remote Similarity	NPD7708	Approved
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD4363	Phase 3
0.6667	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4360	Phase 2
0.6653	Remote Similarity	NPD8091	Phase 3
0.6652	Remote Similarity	NPD7559	Phase 2
0.6652	Remote Similarity	NPD3437	Discontinued
0.6652	Remote Similarity	NPD4002	Approved
0.6652	Remote Similarity	NPD4004	Approved
0.6651	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4981	Phase 2
0.6638	Remote Similarity	NPD7225	Discontinued
0.6637	Remote Similarity	NPD7583	Approved
0.6636	Remote Similarity	NPD5928	Phase 1
0.6636	Remote Similarity	NPD2843	Phase 2
0.6636	Remote Similarity	NPD2845	Phase 2
0.6627	Remote Similarity	NPD7955	Approved
0.6627	Remote Similarity	NPD7956	Approved
0.6625	Remote Similarity	NPD6723	Discontinued
0.6624	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5914	Approved
0.6621	Remote Similarity	NPD4539	Phase 1
0.6618	Remote Similarity	NPD5494	Approved
0.6606	Remote Similarity	NPD2973	Approved
0.6606	Remote Similarity	NPD2974	Approved
0.6606	Remote Similarity	NPD5195	Discontinued
0.6606	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2975	Approved
0.6604	Remote Similarity	NPD7074	Phase 3
0.6601	Remote Similarity	NPD6386	Approved
0.6601	Remote Similarity	NPD6385	Approved
0.6598	Remote Similarity	NPD7417	Discontinued
0.6595	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7186	Phase 3
0.6575	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2248	Approved
0.6571	Remote Similarity	NPD2246	Approved
0.6569	Remote Similarity	NPD6844	Discontinued
0.6568	Remote Similarity	NPD3912	Discontinued
0.6566	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6321	Discontinued
0.6561	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4361	Phase 2
0.656	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7054	Approved
0.6555	Remote Similarity	NPD5710	Approved
0.6555	Remote Similarity	NPD5711	Approved
0.6555	Remote Similarity	NPD6232	Discontinued
0.6553	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7047	Phase 3
0.6552	Remote Similarity	NPD4380	Phase 2
0.655	Remote Similarity	NPD3893	Discontinued
0.6542	Remote Similarity	NPD6962	Phase 2
0.654	Remote Similarity	NPD5938	Phase 3
0.654	Remote Similarity	NPD4505	Phase 1
0.654	Remote Similarity	NPD7473	Discontinued
0.6538	Remote Similarity	NPD5677	Discontinued
0.653	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.653	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7479	Phase 2
0.6526	Remote Similarity	NPD7472	Approved
0.6522	Remote Similarity	NPD955	Approved
0.6518	Remote Similarity	NPD4580	Approved
0.6513	Remote Similarity	NPD1510	Phase 2
0.6509	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3817	Phase 2
0.6495	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3888	Discontinued
0.6493	Remote Similarity	NPD2898	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