NPASS Compound

Structure

CID76478 OpenBabel06191715412D 24 26 0 0 0 0 0 0 0 0999 V2000 2.5981 -1.5000 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 1.0000 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 5.1962 1.0000 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 5.1962 0.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 20 2 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	331.11
Volume:	322.202
LogP:	2.092
LogD:	2.06
LogS:	-3.784
# Rotatable Bonds:	3
TPSA:	90.15
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.715
Synthetic Accessibility Score:	2.705
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.943
MDCK Permeability:	2.5029314201674424e-05
Pgp-inhibitor:	0.071
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.143
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	90.86149597167969%
Volume Distribution (VD):	0.724
Pgp-substrate:	11.023099899291992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.714
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.611
CYP2C9-substrate:	0.85
CYP2D6-inhibitor:	0.151
CYP2D6-substrate:	0.44
CYP3A4-inhibitor:	0.378
CYP3A4-substrate:	0.38

ADMET: Excretion

Clearance (CL):	2.611
Half-life (T1/2):	0.46

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.215
AMES Toxicity:	0.677
Rat Oral Acute Toxicity:	0.625
Maximum Recommended Daily Dose:	0.489
Skin Sensitization:	0.371
Carcinogencity:	0.686
Eye Corrosion:	0.01
Eye Irritation:	0.931
Respiratory Toxicity:	0.362

Download Data

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

Natural Product: NPC76478

Natural Product ID:	NPC76478
*Common Name:**	Citibrasine
IUPAC Name:	1,5-dihydroxy-2,3,4-trimethoxy-10-methylacridin-9-one
Synonyms:	Citibrasine
Standard InCHIKey:	QYPQTPVQPNLXHV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H17NO6/c1-18-11-8(6-5-7-9(11)19)13(20)10-12(18)15(22-2)17(24-4)16(23-3)14(10)21/h5-7,19,21H,1-4H3
SMILES:	Cn1c2c(cccc2O)c(=O)c2c1c(c(c(c2O)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668599
PubChem CID:	19093029
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
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	IC50	=	1200.0	nM	PMID[534774]
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	Ki	=	200.0	nM	PMID[534774]

☑ 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 NPC76478 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	545
0.1-0.2	3238
0.2-0.3	12002
0.3-0.4	5245
0.4-0.5	8606
0.5-0.6	10404
0.6-0.7	2391
0.7-0.8	212
0.8-0.85	22
0.85-0.9	12
0.9-0.95	12
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9798	High Similarity	NPC118189
0.9694	High Similarity	NPC2905
0.9694	High Similarity	NPC148391
0.9646	High Similarity	NPC182853
0.9646	High Similarity	NPC134702
0.9643	High Similarity	NPC114468
0.96	High Similarity	NPC7560
0.9444	High Similarity	NPC268223
0.9343	High Similarity	NPC220241
0.9343	High Similarity	NPC295479
0.9317	High Similarity	NPC285254
0.9272	High Similarity	NPC13249
0.9141	High Similarity	NPC212123
0.9073	High Similarity	NPC157983
0.9073	High Similarity	NPC118154
0.8976	High Similarity	NPC87560
0.8976	High Similarity	NPC195120
0.8873	High Similarity	NPC30749
0.8824	High Similarity	NPC305542
0.8725	High Similarity	NPC474366
0.8636	High Similarity	NPC170333
0.8502	High Similarity	NPC218303
0.8485	Intermediate Similarity	NPC206109
0.8485	Intermediate Similarity	NPC114039
0.8469	Intermediate Similarity	NPC176113
0.8462	Intermediate Similarity	NPC116178
0.8421	Intermediate Similarity	NPC217903
0.8333	Intermediate Similarity	NPC321166
0.8309	Intermediate Similarity	NPC198160
0.8213	Intermediate Similarity	NPC133156
0.8204	Intermediate Similarity	NPC15987
0.8148	Intermediate Similarity	NPC329830
0.8069	Intermediate Similarity	NPC1820
0.801	Intermediate Similarity	NPC234933
0.798	Intermediate Similarity	NPC298320
0.7857	Intermediate Similarity	NPC288759
0.7804	Intermediate Similarity	NPC477825
0.7783	Intermediate Similarity	NPC301292
0.7783	Intermediate Similarity	NPC313112
0.7778	Intermediate Similarity	NPC477826
0.7778	Intermediate Similarity	NPC477827
0.7717	Intermediate Similarity	NPC477828
0.7714	Intermediate Similarity	NPC241263
0.7711	Intermediate Similarity	NPC98416
0.7615	Intermediate Similarity	NPC470481
0.7615	Intermediate Similarity	NPC470482
0.7583	Intermediate Similarity	NPC17677
0.7511	Intermediate Similarity	NPC203373
0.75	Intermediate Similarity	NPC83019
0.7467	Intermediate Similarity	NPC251071
0.7453	Intermediate Similarity	NPC204580
0.7437	Intermediate Similarity	NPC134637
0.7424	Intermediate Similarity	NPC204867
0.7404	Intermediate Similarity	NPC477395
0.7395	Intermediate Similarity	NPC471489
0.7393	Intermediate Similarity	NPC476258
0.7393	Intermediate Similarity	NPC304837
0.7389	Intermediate Similarity	NPC148124
0.7384	Intermediate Similarity	NPC107123
0.7373	Intermediate Similarity	NPC163829
0.7356	Intermediate Similarity	NPC262725
0.7347	Intermediate Similarity	NPC209981
0.7345	Intermediate Similarity	NPC99724
0.7339	Intermediate Similarity	NPC158551
0.7333	Intermediate Similarity	NPC208890
0.7311	Intermediate Similarity	NPC78284
0.7309	Intermediate Similarity	NPC101312
0.7306	Intermediate Similarity	NPC282346
0.73	Intermediate Similarity	NPC299582
0.73	Intermediate Similarity	NPC160100
0.7281	Intermediate Similarity	NPC2173
0.7281	Intermediate Similarity	NPC328700
0.7281	Intermediate Similarity	NPC202771
0.7281	Intermediate Similarity	NPC119818
0.7273	Intermediate Similarity	NPC100573
0.7273	Intermediate Similarity	NPC124714
0.7273	Intermediate Similarity	NPC207873
0.7261	Intermediate Similarity	NPC470480
0.7261	Intermediate Similarity	NPC248903
0.7249	Intermediate Similarity	NPC19175
0.7246	Intermediate Similarity	NPC327005
0.7245	Intermediate Similarity	NPC102003
0.7245	Intermediate Similarity	NPC92722
0.7238	Intermediate Similarity	NPC120239
0.7229	Intermediate Similarity	NPC315914
0.7222	Intermediate Similarity	NPC131266
0.7222	Intermediate Similarity	NPC216769
0.7222	Intermediate Similarity	NPC100971
0.7222	Intermediate Similarity	NPC35763
0.7222	Intermediate Similarity	NPC245382
0.7222	Intermediate Similarity	NPC209487
0.7222	Intermediate Similarity	NPC160113
0.7222	Intermediate Similarity	NPC476220
0.7222	Intermediate Similarity	NPC291802
0.7222	Intermediate Similarity	NPC269451
0.7222	Intermediate Similarity	NPC100263
0.7222	Intermediate Similarity	NPC121522
0.7222	Intermediate Similarity	NPC181209
0.7217	Intermediate Similarity	NPC26928
0.7213	Intermediate Similarity	NPC120513
0.721	Intermediate Similarity	NPC476429
0.7205	Intermediate Similarity	NPC94842
0.7202	Intermediate Similarity	NPC286135
0.72	Intermediate Similarity	NPC472916
0.7198	Intermediate Similarity	NPC85613
0.7198	Intermediate Similarity	NPC5167
0.7194	Intermediate Similarity	NPC15329
0.7194	Intermediate Similarity	NPC131451
0.7194	Intermediate Similarity	NPC183655
0.7194	Intermediate Similarity	NPC287395
0.719	Intermediate Similarity	NPC302807
0.7186	Intermediate Similarity	NPC206238
0.7186	Intermediate Similarity	NPC250557
0.7186	Intermediate Similarity	NPC292214
0.7186	Intermediate Similarity	NPC167091
0.7186	Intermediate Similarity	NPC88645
0.7186	Intermediate Similarity	NPC271779
0.7185	Intermediate Similarity	NPC113455
0.7184	Intermediate Similarity	NPC232386
0.7184	Intermediate Similarity	NPC152680
0.7184	Intermediate Similarity	NPC190783
0.7179	Intermediate Similarity	NPC185031
0.7172	Intermediate Similarity	NPC45291
0.7172	Intermediate Similarity	NPC262623
0.7172	Intermediate Similarity	NPC19980
0.7167	Intermediate Similarity	NPC58209
0.7164	Intermediate Similarity	NPC262286
0.7164	Intermediate Similarity	NPC162869
0.7164	Intermediate Similarity	NPC475267
0.7164	Intermediate Similarity	NPC472914
0.7164	Intermediate Similarity	NPC474836
0.7164	Intermediate Similarity	NPC472910
0.7164	Intermediate Similarity	NPC36852
0.7164	Intermediate Similarity	NPC222814
0.7164	Intermediate Similarity	NPC245758
0.7164	Intermediate Similarity	NPC472911
0.7164	Intermediate Similarity	NPC96167
0.7164	Intermediate Similarity	NPC474208
0.7164	Intermediate Similarity	NPC99597
0.7164	Intermediate Similarity	NPC156057
0.7164	Intermediate Similarity	NPC48208
0.7164	Intermediate Similarity	NPC78225
0.7164	Intermediate Similarity	NPC210084
0.7164	Intermediate Similarity	NPC472913
0.7156	Intermediate Similarity	NPC298449
0.7156	Intermediate Similarity	NPC18306
0.715	Intermediate Similarity	NPC39184
0.715	Intermediate Similarity	NPC130589
0.715	Intermediate Similarity	NPC474815
0.715	Intermediate Similarity	NPC256612
0.715	Intermediate Similarity	NPC134287
0.715	Intermediate Similarity	NPC93653
0.715	Intermediate Similarity	NPC20830
0.715	Intermediate Similarity	NPC2928
0.7149	Intermediate Similarity	NPC16249
0.7143	Intermediate Similarity	NPC93034
0.7143	Intermediate Similarity	NPC119660
0.7143	Intermediate Similarity	NPC119134
0.7143	Intermediate Similarity	NPC207239
0.7137	Intermediate Similarity	NPC477396
0.7137	Intermediate Similarity	NPC82056
0.7136	Intermediate Similarity	NPC199100
0.7136	Intermediate Similarity	NPC268077
0.7136	Intermediate Similarity	NPC39007
0.7136	Intermediate Similarity	NPC180234
0.7136	Intermediate Similarity	NPC120537
0.7136	Intermediate Similarity	NPC101996
0.7136	Intermediate Similarity	NPC161277
0.713	Intermediate Similarity	NPC25961
0.713	Intermediate Similarity	NPC161804
0.7123	Intermediate Similarity	NPC477186
0.7123	Intermediate Similarity	NPC66815
0.7122	Intermediate Similarity	NPC73280
0.7121	Intermediate Similarity	NPC156953
0.7121	Intermediate Similarity	NPC239363
0.7121	Intermediate Similarity	NPC10467
0.7119	Intermediate Similarity	NPC291173
0.7118	Intermediate Similarity	NPC128476
0.7117	Intermediate Similarity	NPC90185
0.7114	Intermediate Similarity	NPC255106
0.7114	Intermediate Similarity	NPC191146
0.7114	Intermediate Similarity	NPC68093
0.7114	Intermediate Similarity	NPC235165
0.7114	Intermediate Similarity	NPC138243
0.7112	Intermediate Similarity	NPC471513
0.7108	Intermediate Similarity	NPC264850
0.7108	Intermediate Similarity	NPC13916
0.7108	Intermediate Similarity	NPC83922
0.7108	Intermediate Similarity	NPC472448
0.7103	Intermediate Similarity	NPC226708
0.7101	Intermediate Similarity	NPC9475
0.71	Intermediate Similarity	NPC160951
0.71	Intermediate Similarity	NPC22519
0.71	Intermediate Similarity	NPC183878
0.71	Intermediate Similarity	NPC472915
0.71	Intermediate Similarity	NPC255350
0.71	Intermediate Similarity	NPC176775
0.71	Intermediate Similarity	NPC274327
0.71	Intermediate Similarity	NPC231018
0.71	Intermediate Similarity	NPC47781

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 NPC76478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	719
0.2-0.3	1131
0.3-0.4	2044
0.4-0.5	2657
0.5-0.6	1762
0.6-0.7	460
0.7-0.8	41
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9898	High Similarity	NPD2899	Discontinued
0.7788	Intermediate Similarity	NPD6625	Approved
0.7523	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5006	Approved
0.7281	Intermediate Similarity	NPD5005	Approved
0.7281	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD1483	Discontinued
0.7241	Intermediate Similarity	NPD5242	Approved
0.7234	Intermediate Similarity	NPD4846	Phase 2
0.7179	Intermediate Similarity	NPD7922	Phase 1
0.7149	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3298	Approved
0.713	Intermediate Similarity	NPD5860	Discontinued
0.7114	Intermediate Similarity	NPD8461	Discontinued
0.71	Intermediate Similarity	NPD2801	Approved
0.7098	Intermediate Similarity	NPD683	Approved
0.7097	Intermediate Similarity	NPD4420	Approved
0.7093	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7263	Phase 2
0.7064	Intermediate Similarity	NPD6874	Approved
0.7014	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6104	Discontinued
0.6982	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7907	Approved
0.6967	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD1934	Approved
0.6957	Remote Similarity	NPD5496	Approved
0.6955	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8067	Phase 3
0.6947	Remote Similarity	NPD1945	Phase 1
0.6941	Remote Similarity	NPD5071	Phase 2
0.6939	Remote Similarity	NPD8367	Approved
0.6909	Remote Similarity	NPD3297	Approved
0.6906	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8492	Approved
0.6893	Remote Similarity	NPD2821	Approved
0.6889	Remote Similarity	NPD4082	Approved
0.6883	Remote Similarity	NPD4111	Phase 1
0.6883	Remote Similarity	NPD4665	Approved
0.6875	Remote Similarity	NPD7048	Phase 3
0.6867	Remote Similarity	NPD6997	Phase 2
0.6864	Remote Similarity	NPD7654	Discontinued
0.6853	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7224	Discontinued
0.6851	Remote Similarity	NPD7223	Discontinued
0.6847	Remote Similarity	NPD2494	Approved
0.6847	Remote Similarity	NPD2493	Approved
0.6847	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD3450	Approved
0.6847	Remote Similarity	NPD3452	Approved
0.6844	Remote Similarity	NPD4596	Phase 1
0.6844	Remote Similarity	NPD7584	Approved
0.6828	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD824	Approved
0.6816	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3472	Approved
0.6814	Remote Similarity	NPD2906	Approved
0.6814	Remote Similarity	NPD2907	Approved
0.6814	Remote Similarity	NPD4022	Approved
0.6786	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3882	Suspended
0.6779	Remote Similarity	NPD5183	Approved
0.6779	Remote Similarity	NPD5186	Approved
0.6773	Remote Similarity	NPD5582	Discontinued
0.6766	Remote Similarity	NPD7279	Phase 2
0.6766	Remote Similarity	NPD7278	Phase 2
0.6757	Remote Similarity	NPD5609	Approved
0.6757	Remote Similarity	NPD5608	Approved
0.6756	Remote Similarity	NPD4582	Approved
0.6756	Remote Similarity	NPD4467	Phase 2
0.6756	Remote Similarity	NPD4583	Approved
0.6756	Remote Similarity	NPD4465	Phase 2
0.6754	Remote Similarity	NPD3372	Discontinued
0.6745	Remote Similarity	NPD7803	Approved
0.6744	Remote Similarity	NPD8053	Approved
0.6744	Remote Similarity	NPD8054	Approved
0.6742	Remote Similarity	NPD4605	Approved
0.6742	Remote Similarity	NPD4604	Approved
0.674	Remote Similarity	NPD7701	Phase 2
0.674	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD5977	Approved
0.6732	Remote Similarity	NPD5353	Approved
0.6732	Remote Similarity	NPD5978	Approved
0.6727	Remote Similarity	NPD4360	Phase 2
0.6727	Remote Similarity	NPD4363	Phase 3
0.6726	Remote Similarity	NPD2339	Phase 3
0.6714	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1220	Phase 1
0.6714	Remote Similarity	NPD6166	Phase 2
0.6714	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5197	Approved
0.6712	Remote Similarity	NPD5196	Approved
0.6712	Remote Similarity	NPD5194	Approved
0.6711	Remote Similarity	NPD4002	Approved
0.6711	Remote Similarity	NPD4004	Approved
0.671	Remote Similarity	NPD7559	Phase 2
0.6706	Remote Similarity	NPD8091	Phase 3
0.6698	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD1221	Approved
0.6697	Remote Similarity	NPD2845	Phase 2
0.6697	Remote Similarity	NPD2843	Phase 2
0.6696	Remote Similarity	NPD4494	Approved
0.6696	Remote Similarity	NPD4492	Approved
0.6695	Remote Similarity	NPD6198	Phase 1
0.6681	Remote Similarity	NPD7047	Phase 3
0.6681	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6385	Approved
0.6667	Remote Similarity	NPD2974	Approved
0.6667	Remote Similarity	NPD2975	Approved
0.6667	Remote Similarity	NPD2973	Approved
0.6667	Remote Similarity	NPD7585	Approved
0.6667	Remote Similarity	NPD6386	Approved
0.6651	Remote Similarity	NPD1898	Discontinued
0.6651	Remote Similarity	NPD3818	Discontinued
0.6651	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1511	Approved
0.6639	Remote Similarity	NPD7186	Phase 3
0.6637	Remote Similarity	NPD4668	Phase 2
0.6636	Remote Similarity	NPD5937	Approved
0.6625	Remote Similarity	NPD6199	Discontinued
0.6623	Remote Similarity	NPD7583	Approved
0.6623	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4361	Phase 2
0.6622	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3793	Phase 3
0.661	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5914	Approved
0.6609	Remote Similarity	NPD8149	Discontinued
0.6606	Remote Similarity	NPD7125	Discontinued
0.6606	Remote Similarity	NPD4515	Suspended
0.6603	Remote Similarity	NPD5494	Approved
0.6603	Remote Similarity	NPD5677	Discontinued
0.6592	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7074	Phase 3
0.6588	Remote Similarity	NPD7708	Approved
0.6584	Remote Similarity	NPD1512	Approved
0.6581	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.658	Remote Similarity	NPD4493	Discontinued
0.658	Remote Similarity	NPD4206	Approved
0.6578	Remote Similarity	NPD4580	Approved
0.6575	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3437	Discontinued
0.6562	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2898	Approved
0.6556	Remote Similarity	NPD4981	Phase 2
0.6553	Remote Similarity	NPD6844	Discontinued
0.6552	Remote Similarity	NPD7225	Discontinued
0.655	Remote Similarity	NPD7043	Discontinued
0.655	Remote Similarity	NPD6296	Discontinued
0.655	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7955	Approved
0.6549	Remote Similarity	NPD7956	Approved
0.6545	Remote Similarity	NPD7886	Phase 2
0.6545	Remote Similarity	NPD7885	Phase 2
0.6545	Remote Similarity	NPD5928	Phase 1
0.6543	Remote Similarity	NPD6723	Discontinued
0.6542	Remote Similarity	NPD7054	Approved
0.654	Remote Similarity	NPD7805	Phase 3
0.654	Remote Similarity	NPD5710	Approved
0.654	Remote Similarity	NPD5711	Approved
0.654	Remote Similarity	NPD6232	Discontinued
0.6538	Remote Similarity	NPD6788	Approved
0.6538	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD4380	Phase 2
0.6537	Remote Similarity	NPD3893	Discontinued
0.6535	Remote Similarity	NPD6644	Discontinued
0.6529	Remote Similarity	NPD1505	Phase 2
0.6526	Remote Similarity	NPD7473	Discontinued
0.6526	Remote Similarity	NPD3446	Phase 1
0.6522	Remote Similarity	NPD7300	Phase 3
0.6522	Remote Similarity	NPD7302	Phase 3
0.6518	Remote Similarity	NPD7417	Discontinued
0.6512	Remote Similarity	NPD7472	Approved
0.6502	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7906	Approved
0.6498	Remote Similarity	NPD7549	Discontinued
0.649	Remote Similarity	NPD3817	Phase 2
0.6485	Remote Similarity	NPD3912	Discontinued
0.6481	Remote Similarity	NPD3888	Discontinued
0.6481	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5488	Discontinued
0.6471	Remote Similarity	NPD3639	Approved
0.6471	Remote Similarity	NPD3640	Phase 3
0.6471	Remote Similarity	NPD3641	Approved
0.6465	Remote Similarity	NPD6020	Phase 2
0.6458	Remote Similarity	NPD3925	Approved
0.6457	Remote Similarity	NPD4539	Phase 1
0.6456	Remote Similarity	NPD5519	Discontinued
0.6456	Remote Similarity	NPD1337	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data