NPASS Compound

Structure

CID13249 OpenBabel06191715342D 26 29 0 0 0 0 0 0 0 0999 V2000 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 5.1962 -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 4.3301 -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 3.4641 -2.0000 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 -0.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 23 2 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.13
Volume:	354.107
LogP:	4.006
LogD:	2.93
LogS:	-3.821
# Rotatable Bonds:	1
TPSA:	80.92
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	3.154
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.801
MDCK Permeability:	2.0415000108187087e-05
Pgp-inhibitor:	0.189
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.494
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	97.89083862304688%
Volume Distribution (VD):	0.461
Pgp-substrate:	2.8760030269622803%

ADMET: Metabolism

CYP1A2-inhibitor:	0.812
CYP1A2-substrate:	0.841
CYP2C19-inhibitor:	0.466
CYP2C19-substrate:	0.448
CYP2C9-inhibitor:	0.829
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.758
CYP2D6-substrate:	0.289
CYP3A4-inhibitor:	0.491
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	1.497
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.649
Drug-inuced Liver Injury (DILI):	0.606
AMES Toxicity:	0.648
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.791
Skin Sensitization:	0.428
Carcinogencity:	0.904
Eye Corrosion:	0.003
Eye Irritation:	0.813
Respiratory Toxicity:	0.721

Download Data

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

Natural Product: NPC13249

Natural Product ID:	NPC13249
*Common Name:**	Pyranofoline
IUPAC Name:	5,10-dihydroxy-12-methoxy-2,2,11-trimethylpyrano[3,2-b]acridin-6-one
Synonyms:	Pyranofoline
Standard InCHIKey:	CTPJHHASTKGQAW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19NO5/c1-20(2)9-8-11-17(24)13-15(19(25-4)18(11)26-20)21(3)14-10(16(13)23)6-5-7-12(14)22/h5-9,22,24H,1-4H3
SMILES:	COc1c2OC(C)(C)C=Cc2c(c2c1n(C)c1c(c2=O)cccc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668600
PubChem CID:	9798626
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
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5476	Hortia arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO7221	Korolkowia sewerzowi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2786	Clematis flammula	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5476	Hortia arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10647	Gentiana lactea	Species	Gentianaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	IC50	=	44000.0	nM	PMID[491474]

☑ 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 NPC13249 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	592
0.1-0.2	3074
0.2-0.3	11763
0.3-0.4	5632
0.4-0.5	8445
0.5-0.6	10136
0.6-0.7	2778
0.7-0.8	225
0.8-0.85	16
0.85-0.9	18
0.9-0.95	15
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9557	High Similarity	NPC7560
0.9453	High Similarity	NPC148391
0.9403	High Similarity	NPC30749
0.9353	High Similarity	NPC305542
0.9279	High Similarity	NPC285254
0.9272	High Similarity	NPC76478
0.9261	High Similarity	NPC2905
0.922	High Similarity	NPC134702
0.9212	High Similarity	NPC114468
0.9167	High Similarity	NPC176113
0.9104	High Similarity	NPC212123
0.9087	High Similarity	NPC118189
0.902	High Similarity	NPC218303
0.8942	High Similarity	NPC182853
0.8932	High Similarity	NPC268223
0.8878	High Similarity	NPC474366
0.8719	High Similarity	NPC15987
0.8654	High Similarity	NPC295479
0.8654	High Similarity	NPC220241
0.8612	High Similarity	NPC116178
0.8607	High Similarity	NPC170333
0.8592	High Similarity	NPC157983
0.8592	High Similarity	NPC118154
0.8571	High Similarity	NPC321166
0.8571	High Similarity	NPC217903
0.8522	High Similarity	NPC234933
0.8498	Intermediate Similarity	NPC87560
0.8498	Intermediate Similarity	NPC195120
0.8462	Intermediate Similarity	NPC198160
0.8454	Intermediate Similarity	NPC301292
0.8454	Intermediate Similarity	NPC313112
0.8365	Intermediate Similarity	NPC133156
0.8357	Intermediate Similarity	NPC288759
0.8295	Intermediate Similarity	NPC329830
0.8276	Intermediate Similarity	NPC114039
0.8276	Intermediate Similarity	NPC206109
0.8213	Intermediate Similarity	NPC241263
0.7961	Intermediate Similarity	NPC1820
0.782	Intermediate Similarity	NPC83019
0.7783	Intermediate Similarity	NPC298320
0.7773	Intermediate Similarity	NPC204580
0.7659	Intermediate Similarity	NPC327005
0.7626	Intermediate Similarity	NPC477825
0.7602	Intermediate Similarity	NPC477827
0.7602	Intermediate Similarity	NPC477826
0.7467	Intermediate Similarity	NPC477828
0.7465	Intermediate Similarity	NPC78284
0.7456	Intermediate Similarity	NPC251071
0.7438	Intermediate Similarity	NPC472448
0.7438	Intermediate Similarity	NPC83922
0.7432	Intermediate Similarity	NPC25961
0.7413	Intermediate Similarity	NPC476981
0.7407	Intermediate Similarity	NPC17677
0.7389	Intermediate Similarity	NPC167678
0.7389	Intermediate Similarity	NPC29876
0.7371	Intermediate Similarity	NPC315914
0.7356	Intermediate Similarity	NPC98416
0.7355	Intermediate Similarity	NPC203373
0.7353	Intermediate Similarity	NPC229632
0.734	Intermediate Similarity	NPC204290
0.734	Intermediate Similarity	NPC476980
0.7324	Intermediate Similarity	NPC469437
0.7322	Intermediate Similarity	NPC477395
0.7311	Intermediate Similarity	NPC476258
0.7311	Intermediate Similarity	NPC304837
0.7304	Intermediate Similarity	NPC259456
0.7303	Intermediate Similarity	NPC107123
0.7291	Intermediate Similarity	NPC204879
0.7289	Intermediate Similarity	NPC470482
0.7289	Intermediate Similarity	NPC470481
0.7282	Intermediate Similarity	NPC472450
0.7282	Intermediate Similarity	NPC275780
0.7282	Intermediate Similarity	NPC239752
0.7269	Intermediate Similarity	NPC38964
0.7268	Intermediate Similarity	NPC261470
0.7264	Intermediate Similarity	NPC262725
0.725	Intermediate Similarity	NPC113455
0.7246	Intermediate Similarity	NPC316292
0.7246	Intermediate Similarity	NPC120593
0.7246	Intermediate Similarity	NPC39091
0.7241	Intermediate Similarity	NPC474681
0.7241	Intermediate Similarity	NPC473272
0.7241	Intermediate Similarity	NPC78225
0.7241	Intermediate Similarity	NPC36852
0.7241	Intermediate Similarity	NPC284820
0.7241	Intermediate Similarity	NPC262286
0.7241	Intermediate Similarity	NPC218313
0.7241	Intermediate Similarity	NPC204867
0.7238	Intermediate Similarity	NPC309692
0.7234	Intermediate Similarity	NPC227033
0.7233	Intermediate Similarity	NPC303460
0.7233	Intermediate Similarity	NPC306321
0.7233	Intermediate Similarity	NPC23298
0.7233	Intermediate Similarity	NPC189473
0.7227	Intermediate Similarity	NPC471489
0.722	Intermediate Similarity	NPC40037
0.722	Intermediate Similarity	NPC258331
0.722	Intermediate Similarity	NPC308943
0.7217	Intermediate Similarity	NPC469439
0.7214	Intermediate Similarity	NPC166201
0.7213	Intermediate Similarity	NPC317567
0.7212	Intermediate Similarity	NPC129578
0.7206	Intermediate Similarity	NPC299582
0.7205	Intermediate Similarity	NPC82056
0.7198	Intermediate Similarity	NPC50960
0.7192	Intermediate Similarity	NPC472455
0.7192	Intermediate Similarity	NPC6633
0.7192	Intermediate Similarity	NPC133970
0.7192	Intermediate Similarity	NPC191146
0.7192	Intermediate Similarity	NPC138243
0.7192	Intermediate Similarity	NPC68093
0.7192	Intermediate Similarity	NPC5322
0.7188	Intermediate Similarity	NPC330683
0.7188	Intermediate Similarity	NPC100573
0.7188	Intermediate Similarity	NPC207873
0.7188	Intermediate Similarity	NPC329567
0.7184	Intermediate Similarity	NPC474150
0.7184	Intermediate Similarity	NPC329760
0.7184	Intermediate Similarity	NPC474162
0.7178	Intermediate Similarity	NPC472915
0.7178	Intermediate Similarity	NPC280937
0.7178	Intermediate Similarity	NPC472408
0.7177	Intermediate Similarity	NPC127082
0.7173	Intermediate Similarity	NPC185031
0.7171	Intermediate Similarity	NPC119209
0.7171	Intermediate Similarity	NPC132385
0.7171	Intermediate Similarity	NPC192686
0.7171	Intermediate Similarity	NPC475784
0.7171	Intermediate Similarity	NPC118256
0.7164	Intermediate Similarity	NPC226973
0.7164	Intermediate Similarity	NPC208043
0.7164	Intermediate Similarity	NPC117579
0.7164	Intermediate Similarity	NPC308451
0.7164	Intermediate Similarity	NPC149614
0.7163	Intermediate Similarity	NPC472449
0.7163	Intermediate Similarity	NPC37870
0.7163	Intermediate Similarity	NPC208890
0.716	Intermediate Similarity	NPC120239
0.716	Intermediate Similarity	NPC58209
0.7157	Intermediate Similarity	NPC217677
0.7157	Intermediate Similarity	NPC165977
0.7157	Intermediate Similarity	NPC181960
0.7157	Intermediate Similarity	NPC52889
0.7156	Intermediate Similarity	NPC46990
0.7156	Intermediate Similarity	NPC310794
0.715	Intermediate Similarity	NPC248638
0.715	Intermediate Similarity	NPC152659
0.715	Intermediate Similarity	NPC236521
0.7149	Intermediate Similarity	NPC160100
0.7149	Intermediate Similarity	NPC298449
0.7143	Intermediate Similarity	NPC256612
0.7143	Intermediate Similarity	NPC160113
0.7143	Intermediate Similarity	NPC472276
0.7143	Intermediate Similarity	NPC57674
0.7143	Intermediate Similarity	NPC256925
0.7143	Intermediate Similarity	NPC234255
0.7143	Intermediate Similarity	NPC472909
0.7143	Intermediate Similarity	NPC113906
0.7143	Intermediate Similarity	NPC20830
0.7143	Intermediate Similarity	NPC476220
0.7143	Intermediate Similarity	NPC200246
0.7143	Intermediate Similarity	NPC117992
0.7143	Intermediate Similarity	NPC37392
0.7143	Intermediate Similarity	NPC472280
0.7143	Intermediate Similarity	NPC152951
0.7143	Intermediate Similarity	NPC230149
0.7143	Intermediate Similarity	NPC168247
0.7137	Intermediate Similarity	NPC119134
0.7136	Intermediate Similarity	NPC57715
0.7136	Intermediate Similarity	NPC61010
0.7136	Intermediate Similarity	NPC474038
0.7136	Intermediate Similarity	NPC234644
0.7136	Intermediate Similarity	NPC134783
0.7136	Intermediate Similarity	NPC474187
0.7136	Intermediate Similarity	NPC266314
0.7131	Intermediate Similarity	NPC477396
0.7131	Intermediate Similarity	NPC209981
0.7131	Intermediate Similarity	NPC476429
0.7129	Intermediate Similarity	NPC8965
0.7122	Intermediate Similarity	NPC250214
0.7122	Intermediate Similarity	NPC152904
0.7122	Intermediate Similarity	NPC95936
0.7122	Intermediate Similarity	NPC184755
0.7122	Intermediate Similarity	NPC74178
0.7117	Intermediate Similarity	NPC286135
0.7117	Intermediate Similarity	NPC202771
0.7117	Intermediate Similarity	NPC2173
0.7117	Intermediate Similarity	NPC328700
0.7117	Intermediate Similarity	NPC119818
0.7115	Intermediate Similarity	NPC234052
0.7114	Intermediate Similarity	NPC306821
0.7114	Intermediate Similarity	NPC302807
0.7114	Intermediate Similarity	NPC473188
0.7114	Intermediate Similarity	NPC179183
0.7114	Intermediate Similarity	NPC101957
0.7114	Intermediate Similarity	NPC120105
0.7113	Intermediate Similarity	NPC154922
0.7109	Intermediate Similarity	NPC85613
0.7109	Intermediate Similarity	NPC475825
0.7109	Intermediate Similarity	NPC223375

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 NPC13249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	712
0.2-0.3	1166
0.3-0.4	2007
0.4-0.5	2645
0.5-0.6	1738
0.6-0.7	486
0.7-0.8	49
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9175	High Similarity	NPD2899	Discontinued
0.7619	Intermediate Similarity	NPD6625	Approved
0.7606	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD3298	Approved
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD8461	Discontinued
0.7385	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD3297	Approved
0.7313	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5860	Discontinued
0.7246	Intermediate Similarity	NPD7922	Phase 1
0.7234	Intermediate Similarity	NPD8067	Phase 3
0.7227	Intermediate Similarity	NPD4846	Phase 2
0.7213	Intermediate Similarity	NPD8367	Approved
0.7204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2906	Approved
0.7188	Intermediate Similarity	NPD2907	Approved
0.7178	Intermediate Similarity	NPD1483	Discontinued
0.7174	Intermediate Similarity	NPD5496	Approved
0.7166	Intermediate Similarity	NPD8492	Approved
0.7162	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD3783	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6874	Approved
0.7117	Intermediate Similarity	NPD5005	Approved
0.7117	Intermediate Similarity	NPD5006	Approved
0.7112	Intermediate Similarity	NPD7907	Approved
0.7094	Intermediate Similarity	NPD2801	Approved
0.7093	Intermediate Similarity	NPD1945	Phase 1
0.7075	Intermediate Similarity	NPD6104	Discontinued
0.7067	Intermediate Similarity	NPD7263	Phase 2
0.7054	Intermediate Similarity	NPD5102	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7585	Approved
0.7035	Intermediate Similarity	NPD6593	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4363	Phase 3
0.7032	Intermediate Similarity	NPD4360	Phase 2
0.7026	Intermediate Similarity	NPD4111	Phase 1
0.7026	Intermediate Similarity	NPD4665	Approved
0.7009	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD7654	Discontinued
0.6996	Remote Similarity	NPD2493	Approved
0.6996	Remote Similarity	NPD3450	Approved
0.6996	Remote Similarity	NPD3452	Approved
0.6996	Remote Similarity	NPD2494	Approved
0.6991	Remote Similarity	NPD7583	Approved
0.6978	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6199	Discontinued
0.6968	Remote Similarity	NPD2973	Approved
0.6968	Remote Similarity	NPD2975	Approved
0.6968	Remote Similarity	NPD2974	Approved
0.6962	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4082	Approved
0.6951	Remote Similarity	NPD2339	Phase 3
0.6942	Remote Similarity	NPD7048	Phase 3
0.6937	Remote Similarity	NPD4420	Approved
0.6936	Remote Similarity	NPD6997	Phase 2
0.6927	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5494	Approved
0.6923	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7223	Discontinued
0.692	Remote Similarity	NPD7224	Discontinued
0.6916	Remote Similarity	NPD4596	Phase 1
0.691	Remote Similarity	NPD6198	Phase 1
0.6907	Remote Similarity	NPD7279	Phase 2
0.6907	Remote Similarity	NPD7278	Phase 2
0.6903	Remote Similarity	NPD4582	Approved
0.6903	Remote Similarity	NPD4583	Approved
0.6892	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3472	Approved
0.6886	Remote Similarity	NPD4022	Approved
0.6886	Remote Similarity	NPD7701	Phase 2
0.6878	Remote Similarity	NPD1934	Approved
0.6875	Remote Similarity	NPD4580	Approved
0.6867	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5937	Approved
0.6858	Remote Similarity	NPD4004	Approved
0.6858	Remote Similarity	NPD4002	Approved
0.6854	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4361	Phase 2
0.6847	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4981	Phase 2
0.6828	Remote Similarity	NPD4465	Phase 2
0.6828	Remote Similarity	NPD4467	Phase 2
0.6826	Remote Similarity	NPD3372	Discontinued
0.6824	Remote Similarity	NPD8149	Discontinued
0.6822	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD683	Approved
0.6796	Remote Similarity	NPD6844	Discontinued
0.6791	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5071	Phase 2
0.6778	Remote Similarity	NPD7186	Phase 3
0.6773	Remote Similarity	NPD5928	Phase 1
0.6767	Remote Similarity	NPD4494	Approved
0.6767	Remote Similarity	NPD4492	Approved
0.6761	Remote Similarity	NPD3446	Phase 1
0.6756	Remote Similarity	NPD8285	Discontinued
0.6753	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7047	Phase 3
0.6751	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7803	Approved
0.6741	Remote Similarity	NPD4604	Approved
0.6741	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD4605	Approved
0.6736	Remote Similarity	NPD3925	Approved
0.673	Remote Similarity	NPD2821	Approved
0.6729	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7549	Discontinued
0.6727	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6166	Phase 2
0.6714	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4380	Phase 2
0.6699	Remote Similarity	NPD3882	Suspended
0.6698	Remote Similarity	NPD3793	Phase 3
0.6696	Remote Similarity	NPD7043	Discontinued
0.6696	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6644	Discontinued
0.6681	Remote Similarity	NPD5914	Approved
0.6667	Remote Similarity	NPD8054	Approved
0.6667	Remote Similarity	NPD8053	Approved
0.6652	Remote Similarity	NPD1898	Discontinued
0.6652	Remote Similarity	NPD4493	Discontinued
0.6652	Remote Similarity	NPD7906	Approved
0.6651	Remote Similarity	NPD5353	Approved
0.6651	Remote Similarity	NPD3818	Discontinued
0.6651	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1511	Approved
0.6637	Remote Similarity	NPD4668	Phase 2
0.6637	Remote Similarity	NPD5197	Approved
0.6637	Remote Similarity	NPD5194	Approved
0.6637	Remote Similarity	NPD5196	Approved
0.6636	Remote Similarity	NPD2248	Approved
0.6636	Remote Similarity	NPD2246	Approved
0.6636	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7225	Discontinued
0.6621	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5710	Approved
0.662	Remote Similarity	NPD5844	Phase 1
0.662	Remote Similarity	NPD5711	Approved
0.662	Remote Similarity	NPD5183	Approved
0.662	Remote Similarity	NPD7054	Approved
0.662	Remote Similarity	NPD5186	Approved
0.6618	Remote Similarity	NPD6585	Discontinued
0.6618	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3893	Discontinued
0.6607	Remote Similarity	NPD7125	Discontinued
0.6606	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4515	Suspended
0.6604	Remote Similarity	NPD5677	Discontinued
0.6598	Remote Similarity	NPD1505	Phase 2
0.6592	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7074	Phase 3
0.659	Remote Similarity	NPD7472	Approved
0.6589	Remote Similarity	NPD7708	Approved
0.6587	Remote Similarity	NPD5889	Approved
0.6587	Remote Similarity	NPD5890	Approved
0.6586	Remote Similarity	NPD7417	Discontinued
0.6585	Remote Similarity	NPD1512	Approved
0.6579	Remote Similarity	NPD5457	Discontinued
0.6576	Remote Similarity	NPD8091	Phase 3
0.6571	Remote Similarity	NPD3817	Phase 2
0.6571	Remote Similarity	NPD5978	Approved
0.6571	Remote Similarity	NPD5977	Approved
0.6568	Remote Similarity	NPD7559	Phase 2
0.6553	Remote Similarity	NPD3888	Discontinued
0.655	Remote Similarity	NPD7956	Approved
0.655	Remote Similarity	NPD7955	Approved
0.6547	Remote Similarity	NPD2845	Phase 2
0.6547	Remote Similarity	NPD2843	Phase 2
0.6546	Remote Similarity	NPD7886	Phase 2
0.6546	Remote Similarity	NPD7885	Phase 2
0.6546	Remote Similarity	NPD7560	Approved
0.6542	Remote Similarity	NPD6232	Discontinued
0.654	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.654	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5608	Approved
0.6535	Remote Similarity	NPD5609	Approved
0.6532	Remote Similarity	NPD4663	Approved
0.653	Remote Similarity	NPD7039	Approved
0.653	Remote Similarity	NPD7038	Approved
0.6528	Remote Similarity	NPD7473	Discontinued
0.6525	Remote Similarity	NPD4455	Discontinued
0.6524	Remote Similarity	NPD4859	Phase 1
0.6522	Remote Similarity	NPD3057	Approved
0.6518	Remote Similarity	NPD2488	Approved
0.6518	Remote Similarity	NPD2490	Approved
0.6511	Remote Similarity	NPD5676	Approved
0.6509	Remote Similarity	NPD955	Approved
0.6509	Remote Similarity	NPD7075	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data