NPASS Compound

Structure

CID285254 OpenBabel06191716092D 31 33 0 0 0 0 0 0 0 0999 V2000 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 0.8660 -1.5000 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 -1.7321 2.0000 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 2.5981 4.5000 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 3.4641 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 3.4641 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 2.5981 0.5000 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 -0.8660 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 -0.0000 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 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 26 1 0 0 0 0 6 31 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 15 18 2 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 20 2 0 0 0 0 17 27 1 0 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 22 28 1 0 0 0 0 23 25 2 0 0 0 0 23 29 1 0 0 0 0 24 30 2 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	423.2
Volume:	446.506
LogP:	5.949
LogD:	3.128
LogS:	-3.112
# Rotatable Bonds:	5
TPSA:	91.92
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.404
Synthetic Accessibility Score:	3.331
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.798
MDCK Permeability:	1.1891360372828785e-05
Pgp-inhibitor:	0.836
Pgp-substrate:	0.655
Human Intestinal Absorption (HIA):	0.36
20% Bioavailability (F20%):	0.701
30% Bioavailability (F30%):	0.084

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	83.96500396728516%
Volume Distribution (VD):	0.634
Pgp-substrate:	12.507452011108398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.496
CYP1A2-substrate:	0.391
CYP2C19-inhibitor:	0.8
CYP2C19-substrate:	0.138
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.587
CYP2D6-substrate:	0.245
CYP3A4-inhibitor:	0.158
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	3.927
Half-life (T1/2):	0.236

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.8
Drug-inuced Liver Injury (DILI):	0.174
AMES Toxicity:	0.62
Rat Oral Acute Toxicity:	0.31
Maximum Recommended Daily Dose:	0.236
Skin Sensitization:	0.777
Carcinogencity:	0.503
Eye Corrosion:	0.003
Eye Irritation:	0.867
Respiratory Toxicity:	0.384

Download Data

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

Natural Product: NPC285254

Natural Product ID:	NPC285254
*Common Name:**	1,3,5-Trihydroxy-4-Methoxy-10-Methyl-2,8-Bis(3-Methylbut-2-Enyl)Acridin-9-One
IUPAC Name:	1,3,5-trihydroxy-4-methoxy-10-methyl-2,8-bis(3-methylbut-2-enyl)acridin-9-one
Synonyms:
Standard InCHIKey:	LICNIJQEAUQKSD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H29NO5/c1-13(2)7-9-15-10-12-17(27)20-18(15)24(30)19-21(26(20)5)25(31-6)23(29)16(22(19)28)11-8-14(3)4/h7-8,10,12,27-29H,9,11H2,1-6H3
SMILES:	COc1c(O)c(CC=C(C)C)c(c2c1n(C)c1c(c2=O)c(CC=C(C)C)ccc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668597
PubChem CID:	53316985
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]
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]
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]

☑ 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	=	2500.0	nM	PMID[457130]
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	Ki	=	500.0	nM	PMID[457130]

☑ 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 NPC285254 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	558
0.1-0.2	2862
0.2-0.3	11835
0.3-0.4	5799
0.4-0.5	8519
0.5-0.6	10781
0.6-0.7	2063
0.7-0.8	232
0.8-0.85	21
0.85-0.9	17
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC7560
0.9403	High Similarity	NPC2905
0.9353	High Similarity	NPC114468
0.9317	High Similarity	NPC76478
0.9307	High Similarity	NPC148391
0.9279	High Similarity	NPC13249
0.9265	High Similarity	NPC134702
0.913	High Similarity	NPC118189
0.8986	High Similarity	NPC182853
0.896	High Similarity	NPC212123
0.8861	High Similarity	NPC133156
0.8792	High Similarity	NPC268223
0.8738	High Similarity	NPC474366
0.8702	High Similarity	NPC30749
0.8696	High Similarity	NPC295479
0.8696	High Similarity	NPC220241
0.8654	High Similarity	NPC305542
0.8557	High Similarity	NPC170333
0.8483	Intermediate Similarity	NPC176113
0.8458	Intermediate Similarity	NPC118154
0.8458	Intermediate Similarity	NPC157983
0.8364	Intermediate Similarity	NPC195120
0.8364	Intermediate Similarity	NPC87560
0.8341	Intermediate Similarity	NPC218303
0.8216	Intermediate Similarity	NPC116178
0.8178	Intermediate Similarity	NPC217903
0.8137	Intermediate Similarity	NPC114039
0.8137	Intermediate Similarity	NPC206109
0.8093	Intermediate Similarity	NPC321166
0.8066	Intermediate Similarity	NPC198160
0.8048	Intermediate Similarity	NPC15987
0.7943	Intermediate Similarity	NPC17677
0.7919	Intermediate Similarity	NPC329830
0.7857	Intermediate Similarity	NPC234933
0.7804	Intermediate Similarity	NPC301292
0.7804	Intermediate Similarity	NPC313112
0.7751	Intermediate Similarity	NPC78284
0.7746	Intermediate Similarity	NPC471489
0.774	Intermediate Similarity	NPC1820
0.7734	Intermediate Similarity	NPC298320
0.771	Intermediate Similarity	NPC288759
0.7696	Intermediate Similarity	NPC207873
0.7696	Intermediate Similarity	NPC100573
0.757	Intermediate Similarity	NPC241263
0.7568	Intermediate Similarity	NPC298449
0.7566	Intermediate Similarity	NPC251071
0.7557	Intermediate Similarity	NPC470481
0.7557	Intermediate Similarity	NPC470482
0.7545	Intermediate Similarity	NPC25961
0.7534	Intermediate Similarity	NPC90185
0.7489	Intermediate Similarity	NPC308943
0.7476	Intermediate Similarity	NPC320088
0.7426	Intermediate Similarity	NPC477395
0.7409	Intermediate Similarity	NPC132385
0.7403	Intermediate Similarity	NPC315914
0.7391	Intermediate Similarity	NPC98416
0.7391	Intermediate Similarity	NPC200888
0.7386	Intermediate Similarity	NPC134637
0.7381	Intermediate Similarity	NPC33902
0.7381	Intermediate Similarity	NPC276674
0.738	Intermediate Similarity	NPC94842
0.7361	Intermediate Similarity	NPC193906
0.7361	Intermediate Similarity	NPC23080
0.7361	Intermediate Similarity	NPC83019
0.7359	Intermediate Similarity	NPC470480
0.7355	Intermediate Similarity	NPC302807
0.7344	Intermediate Similarity	NPC270515
0.7342	Intermediate Similarity	NPC46990
0.7342	Intermediate Similarity	NPC477825
0.7339	Intermediate Similarity	NPC227033
0.7333	Intermediate Similarity	NPC107123
0.7321	Intermediate Similarity	NPC477826
0.7321	Intermediate Similarity	NPC477827
0.7315	Intermediate Similarity	NPC204580
0.7314	Intermediate Similarity	NPC317567
0.7277	Intermediate Similarity	NPC208890
0.7269	Intermediate Similarity	NPC304837
0.7269	Intermediate Similarity	NPC477828
0.7269	Intermediate Similarity	NPC476258
0.7257	Intermediate Similarity	NPC55470
0.7252	Intermediate Similarity	NPC222561
0.725	Intermediate Similarity	NPC15406
0.7235	Intermediate Similarity	NPC161804
0.7229	Intermediate Similarity	NPC209981
0.7227	Intermediate Similarity	NPC2173
0.7227	Intermediate Similarity	NPC328700
0.7227	Intermediate Similarity	NPC286135
0.7227	Intermediate Similarity	NPC119818
0.7227	Intermediate Similarity	NPC202771
0.7208	Intermediate Similarity	NPC113455
0.7206	Intermediate Similarity	NPC228785
0.7206	Intermediate Similarity	NPC14353
0.7206	Intermediate Similarity	NPC56085
0.7203	Intermediate Similarity	NPC185031
0.7194	Intermediate Similarity	NPC101312
0.7192	Intermediate Similarity	NPC204867
0.719	Intermediate Similarity	NPC327005
0.7189	Intermediate Similarity	NPC282346
0.7184	Intermediate Similarity	NPC220313
0.7171	Intermediate Similarity	NPC61010
0.7171	Intermediate Similarity	NPC40491
0.7171	Intermediate Similarity	NPC278052
0.7169	Intermediate Similarity	NPC207239
0.7163	Intermediate Similarity	NPC239775
0.7162	Intermediate Similarity	NPC82056
0.716	Intermediate Similarity	NPC477396
0.7157	Intermediate Similarity	NPC100123
0.715	Intermediate Similarity	NPC275780
0.715	Intermediate Similarity	NPC472450
0.715	Intermediate Similarity	NPC239752
0.7143	Intermediate Similarity	NPC473188
0.7137	Intermediate Similarity	NPC471513
0.7136	Intermediate Similarity	NPC262725
0.7131	Intermediate Similarity	NPC316292
0.713	Intermediate Similarity	NPC294244
0.713	Intermediate Similarity	NPC226708
0.713	Intermediate Similarity	NPC196231
0.7129	Intermediate Similarity	NPC232386
0.7129	Intermediate Similarity	NPC190783
0.7129	Intermediate Similarity	NPC152680
0.7125	Intermediate Similarity	NPC41501
0.7122	Intermediate Similarity	NPC320359
0.7119	Intermediate Similarity	NPC211215
0.7119	Intermediate Similarity	NPC120239
0.7116	Intermediate Similarity	NPC474904
0.7115	Intermediate Similarity	NPC118274
0.7115	Intermediate Similarity	NPC168753
0.7115	Intermediate Similarity	NPC39091
0.7109	Intermediate Similarity	NPC190461
0.7109	Intermediate Similarity	NPC472163
0.7108	Intermediate Similarity	NPC217677
0.7108	Intermediate Similarity	NPC300727
0.7108	Intermediate Similarity	NPC241904
0.7108	Intermediate Similarity	NPC165977
0.7108	Intermediate Similarity	NPC78225
0.7103	Intermediate Similarity	NPC18306
0.7101	Intermediate Similarity	NPC7483
0.7101	Intermediate Similarity	NPC160113
0.7101	Intermediate Similarity	NPC236521
0.7101	Intermediate Similarity	NPC189473
0.7101	Intermediate Similarity	NPC476220
0.7101	Intermediate Similarity	NPC23298
0.7101	Intermediate Similarity	NPC236132
0.7101	Intermediate Similarity	NPC248638
0.7101	Intermediate Similarity	NPC152659
0.7087	Intermediate Similarity	NPC474187
0.7087	Intermediate Similarity	NPC32694
0.7087	Intermediate Similarity	NPC311740
0.7085	Intermediate Similarity	NPC163829
0.7085	Intermediate Similarity	NPC268077
0.7078	Intermediate Similarity	NPC477393
0.7078	Intermediate Similarity	NPC24228
0.7074	Intermediate Similarity	NPC38964
0.7074	Intermediate Similarity	NPC240684
0.7073	Intermediate Similarity	NPC476242
0.7073	Intermediate Similarity	NPC299582
0.7071	Intermediate Similarity	NPC154922
0.7067	Intermediate Similarity	NPC326520
0.7059	Intermediate Similarity	NPC274730
0.7059	Intermediate Similarity	NPC191146
0.7059	Intermediate Similarity	NPC68093
0.7059	Intermediate Similarity	NPC142339
0.7054	Intermediate Similarity	NPC80472
0.7054	Intermediate Similarity	NPC158551
0.7053	Intermediate Similarity	NPC264850
0.7053	Intermediate Similarity	NPC229632
0.7053	Intermediate Similarity	NPC25152
0.7053	Intermediate Similarity	NPC13916
0.7051	Intermediate Similarity	NPC19175
0.7048	Intermediate Similarity	NPC285941
0.7045	Intermediate Similarity	NPC215098
0.7045	Intermediate Similarity	NPC14622
0.7045	Intermediate Similarity	NPC71124
0.7045	Intermediate Similarity	NPC124302
0.7045	Intermediate Similarity	NPC46744
0.7045	Intermediate Similarity	NPC70290
0.7045	Intermediate Similarity	NPC73020
0.7039	Intermediate Similarity	NPC475886
0.7039	Intermediate Similarity	NPC36217
0.7039	Intermediate Similarity	NPC84571
0.7039	Intermediate Similarity	NPC45146
0.7039	Intermediate Similarity	NPC235018
0.7039	Intermediate Similarity	NPC474287
0.7033	Intermediate Similarity	NPC37870
0.7033	Intermediate Similarity	NPC170245
0.7033	Intermediate Similarity	NPC203373
0.7033	Intermediate Similarity	NPC472449
0.7032	Intermediate Similarity	NPC162653
0.7031	Intermediate Similarity	NPC290227
0.7027	Intermediate Similarity	NPC151470
0.7027	Intermediate Similarity	NPC201055
0.7027	Intermediate Similarity	NPC64576
0.7027	Intermediate Similarity	NPC254045
0.7025	Intermediate Similarity	NPC119134
0.7024	Intermediate Similarity	NPC136674
0.7024	Intermediate Similarity	NPC236796
0.7024	Intermediate Similarity	NPC36852
0.7024	Intermediate Similarity	NPC262286
0.7019	Intermediate Similarity	NPC306555
0.7019	Intermediate Similarity	NPC205421

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 NPC285254 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	687
0.2-0.3	1184
0.3-0.4	2007
0.4-0.5	2673
0.5-0.6	1784
0.6-0.7	446
0.7-0.8	36
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.922	High Similarity	NPD2899	Discontinued
0.7729	Intermediate Similarity	NPD6625	Approved
0.7652	Intermediate Similarity	NPD7922	Phase 1
0.7454	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD8067	Phase 3
0.7314	Intermediate Similarity	NPD8367	Approved
0.7265	Intermediate Similarity	NPD8492	Approved
0.724	Intermediate Similarity	NPD3298	Approved
0.7227	Intermediate Similarity	NPD5006	Approved
0.7227	Intermediate Similarity	NPD5005	Approved
0.7208	Intermediate Similarity	NPD1483	Discontinued
0.7206	Intermediate Similarity	NPD8461	Discontinued
0.7174	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6593	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5860	Discontinued
0.7072	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7907	Approved
0.7056	Intermediate Similarity	NPD5496	Approved
0.7045	Intermediate Similarity	NPD5197	Approved
0.7045	Intermediate Similarity	NPD4420	Approved
0.7045	Intermediate Similarity	NPD5196	Approved
0.7045	Intermediate Similarity	NPD5194	Approved
0.7043	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3452	Approved
0.7027	Intermediate Similarity	NPD3450	Approved
0.7027	Intermediate Similarity	NPD2493	Approved
0.7027	Intermediate Similarity	NPD2494	Approved
0.7022	Intermediate Similarity	NPD7263	Phase 2
0.7019	Intermediate Similarity	NPD5242	Approved
0.7014	Intermediate Similarity	NPD3297	Approved
0.7009	Intermediate Similarity	NPD7278	Phase 2
0.7009	Intermediate Similarity	NPD7279	Phase 2
0.6983	Remote Similarity	NPD4111	Phase 1
0.6983	Remote Similarity	NPD4665	Approved
0.6974	Remote Similarity	NPD1945	Phase 1
0.6971	Remote Similarity	NPD4846	Phase 2
0.6968	Remote Similarity	NPD4668	Phase 2
0.6964	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7654	Discontinued
0.6951	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4583	Approved
0.6933	Remote Similarity	NPD4582	Approved
0.6916	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7048	Phase 3
0.6894	Remote Similarity	NPD6997	Phase 2
0.6889	Remote Similarity	NPD4002	Approved
0.6889	Remote Similarity	NPD4004	Approved
0.6878	Remote Similarity	NPD2801	Approved
0.6869	Remote Similarity	NPD6104	Discontinued
0.6861	Remote Similarity	NPD5608	Approved
0.6861	Remote Similarity	NPD5609	Approved
0.6858	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD8149	Discontinued
0.6847	Remote Similarity	NPD2974	Approved
0.6847	Remote Similarity	NPD2975	Approved
0.6847	Remote Similarity	NPD2973	Approved
0.6844	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7701	Phase 2
0.6842	Remote Similarity	NPD4082	Approved
0.6818	Remote Similarity	NPD5937	Approved
0.6816	Remote Similarity	NPD5071	Phase 2
0.6798	Remote Similarity	NPD4596	Phase 1
0.6796	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6874	Approved
0.6784	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5195	Discontinued
0.6771	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4022	Approved
0.6769	Remote Similarity	NPD2906	Approved
0.6769	Remote Similarity	NPD3472	Approved
0.6769	Remote Similarity	NPD2907	Approved
0.6765	Remote Similarity	NPD3925	Approved
0.6763	Remote Similarity	NPD5978	Approved
0.6763	Remote Similarity	NPD5977	Approved
0.6756	Remote Similarity	NPD4580	Approved
0.6748	Remote Similarity	NPD1934	Approved
0.674	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6232	Discontinued
0.673	Remote Similarity	NPD5710	Approved
0.673	Remote Similarity	NPD5711	Approved
0.6714	Remote Similarity	NPD7473	Discontinued
0.6711	Remote Similarity	NPD4465	Phase 2
0.6711	Remote Similarity	NPD4467	Phase 2
0.671	Remote Similarity	NPD3372	Discontinued
0.6709	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7047	Phase 3
0.6708	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6723	Discontinued
0.6707	Remote Similarity	NPD5488	Discontinued
0.6697	Remote Similarity	NPD8053	Approved
0.6697	Remote Similarity	NPD2488	Approved
0.6697	Remote Similarity	NPD8054	Approved
0.6697	Remote Similarity	NPD2490	Approved
0.6696	Remote Similarity	NPD7300	Phase 3
0.6696	Remote Similarity	NPD7302	Phase 3
0.6696	Remote Similarity	NPD4859	Phase 1
0.6696	Remote Similarity	NPD4605	Approved
0.6696	Remote Similarity	NPD4604	Approved
0.6682	Remote Similarity	NPD4360	Phase 2
0.6682	Remote Similarity	NPD2821	Approved
0.6682	Remote Similarity	NPD4363	Phase 3
0.6682	Remote Similarity	NPD7906	Approved
0.6681	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD683	Approved
0.6667	Remote Similarity	NPD1220	Phase 1
0.6667	Remote Similarity	NPD2898	Approved
0.6667	Remote Similarity	NPD8091	Phase 3
0.6653	Remote Similarity	NPD7292	Approved
0.6653	Remote Similarity	NPD4981	Phase 2
0.6652	Remote Similarity	NPD4492	Approved
0.6652	Remote Similarity	NPD7584	Approved
0.6652	Remote Similarity	NPD4494	Approved
0.6652	Remote Similarity	NPD7225	Discontinued
0.6651	Remote Similarity	NPD1221	Approved
0.6651	Remote Similarity	NPD6020	Phase 2
0.6651	Remote Similarity	NPD3793	Phase 3
0.6641	Remote Similarity	NPD7803	Approved
0.6622	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4493	Discontinued
0.6608	Remote Similarity	NPD2339	Phase 3
0.6598	Remote Similarity	NPD7224	Discontinued
0.6598	Remote Similarity	NPD7223	Discontinued
0.659	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6199	Discontinued
0.658	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4361	Phase 2
0.6578	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5183	Approved
0.6573	Remote Similarity	NPD5186	Approved
0.6568	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3893	Discontinued
0.6565	Remote Similarity	NPD6644	Discontinued
0.6561	Remote Similarity	NPD4663	Approved
0.6557	Remote Similarity	NPD5494	Approved
0.6552	Remote Similarity	NPD7585	Approved
0.655	Remote Similarity	NPD3448	Approved
0.655	Remote Similarity	NPD3515	Approved
0.655	Remote Similarity	NPD3516	Approved
0.655	Remote Similarity	NPD2491	Approved
0.6544	Remote Similarity	NPD7479	Phase 2
0.654	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD6807	Phase 3
0.653	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD3437	Discontinued
0.6525	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD824	Approved
0.6518	Remote Similarity	NPD5968	Phase 3
0.6512	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6166	Phase 2
0.6511	Remote Similarity	NPD7301	Phase 3
0.6509	Remote Similarity	NPD7043	Discontinued
0.6509	Remote Similarity	NPD7583	Approved
0.6505	Remote Similarity	NPD3640	Phase 3
0.6505	Remote Similarity	NPD3641	Approved
0.6505	Remote Similarity	NPD3639	Approved
0.6504	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD5928	Phase 1
0.65	Remote Similarity	NPD4577	Approved
0.65	Remote Similarity	NPD4578	Approved
0.6493	Remote Similarity	NPD3882	Suspended
0.6489	Remote Similarity	NPD7125	Discontinued
0.6489	Remote Similarity	NPD5610	Approved
0.6486	Remote Similarity	NPD7708	Approved
0.6483	Remote Similarity	NPD4455	Discontinued
0.6481	Remote Similarity	NPD5938	Phase 3
0.6481	Remote Similarity	NPD3446	Phase 1
0.6478	Remote Similarity	NPD3057	Approved
0.6473	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5676	Approved
0.6463	Remote Similarity	NPD6777	Approved
0.6463	Remote Similarity	NPD6780	Approved
0.6463	Remote Similarity	NPD6776	Approved
0.6463	Remote Similarity	NPD6778	Approved
0.6463	Remote Similarity	NPD6781	Approved
0.6463	Remote Similarity	NPD6782	Approved
0.6463	Remote Similarity	NPD6779	Approved
0.6457	Remote Similarity	NPD1898	Discontinued
0.6452	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7497	Discontinued
0.6448	Remote Similarity	NPD7956	Approved
0.6448	Remote Similarity	NPD7955	Approved
0.6446	Remote Similarity	NPD3912	Discontinued
0.6446	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD5353	Approved
0.6444	Remote Similarity	NPD6198	Phase 1
0.6441	Remote Similarity	NPD3888	Discontinued
0.6441	Remote Similarity	NPD7827	Phase 1
0.6439	Remote Similarity	NPD1511	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