NPASS Compound

Structure

CID212123 OpenBabel06191716002D 25 27 0 0 0 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -4.3301 0.5000 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 1.7321 2.0000 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 -1.5000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 1.5000 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 -1.7321 2.0000 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 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 -0.8660 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 0.0000 0.0000 0.0000 N 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 -1.7321 3.0000 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 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 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 13 1 0 0 0 0 7 14 2 0 0 0 0 8 9 1 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 21 1 0 0 0 0 20 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	339.15
Volume:	353.873
LogP:	4.39
LogD:	3.065
LogS:	-3.572
# Rotatable Bonds:	3
TPSA:	71.69
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	2.87
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.777
MDCK Permeability:	1.1833467397082131e-05
Pgp-inhibitor:	0.125
Pgp-substrate:	0.158
Human Intestinal Absorption (HIA):	0.101
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	91.166748046875%
Volume Distribution (VD):	0.661
Pgp-substrate:	4.625767707824707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.939
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.888
CYP2C19-substrate:	0.209
CYP2C9-inhibitor:	0.828
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.817
CYP2D6-substrate:	0.611
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	6.473
Half-life (T1/2):	0.374

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.524
AMES Toxicity:	0.832
Rat Oral Acute Toxicity:	0.178
Maximum Recommended Daily Dose:	0.865
Skin Sensitization:	0.77
Carcinogencity:	0.827
Eye Corrosion:	0.005
Eye Irritation:	0.935
Respiratory Toxicity:	0.624

Download Data

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

Natural Product: NPC212123

Natural Product ID:	NPC212123
*Common Name:**	Glycocitrine I
IUPAC Name:	1,5-dihydroxy-3-methoxy-10-methyl-4-(3-methylbut-2-enyl)acridin-9-one
Synonyms:	glycocitrine I
Standard InCHIKey:	ICOVYJLPIYGGGL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H21NO4/c1-11(2)8-9-12-16(25-4)10-15(23)17-19(12)21(3)18-13(20(17)24)6-5-7-14(18)22/h5-8,10,22-23H,9H2,1-4H3
SMILES:	COc1cc(O)c2c(c1CC=C(C)C)n(C)c1c(c2=O)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508186
PubChem CID:	11724762
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
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29975532]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27785	Atalantia buxifolia	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	7

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[503819]
NPT319	Cell Line	B16	Mus musculus	IC50	>	40000.0	nM	PMID[503819]
NPT1353	Cell Line	CCRF-HSB-2	Homo sapiens	IC50	>	40000.0	nM	PMID[503819]
NPT1354	Cell Line	TGBC11TKB	Homo sapiens	IC50	>	40000.0	nM	PMID[503819]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[503820]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[503820]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[503820]

☑ 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 NPC212123 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	499
0.1-0.2	3079
0.2-0.3	11322
0.3-0.4	5478
0.4-0.5	8908
0.5-0.6	10685
0.6-0.7	2373
0.7-0.8	301
0.8-0.85	9
0.85-0.9	21
0.9-0.95	17
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC305542
0.9579	High Similarity	NPC30749
0.9524	High Similarity	NPC474366
0.9454	High Similarity	NPC170333
0.9326	High Similarity	NPC148391
0.9271	High Similarity	NPC218303
0.9239	High Similarity	NPC7560
0.9227	High Similarity	NPC176113
0.9184	High Similarity	NPC182853
0.9141	High Similarity	NPC76478
0.9128	High Similarity	NPC2905
0.9104	High Similarity	NPC13249
0.9086	High Similarity	NPC134702
0.9081	High Similarity	NPC114039
0.9081	High Similarity	NPC206109
0.9077	High Similarity	NPC114468
0.8964	High Similarity	NPC198160
0.896	High Similarity	NPC285254
0.8958	High Similarity	NPC133156
0.8953	High Similarity	NPC15987
0.895	High Similarity	NPC118189
0.8878	High Similarity	NPC220241
0.8878	High Similarity	NPC295479
0.8832	High Similarity	NPC116178
0.8788	High Similarity	NPC321166
0.8788	High Similarity	NPC268223
0.8788	High Similarity	NPC217903
0.8743	High Similarity	NPC234933
0.8624	High Similarity	NPC1820
0.8614	High Similarity	NPC87560
0.8614	High Similarity	NPC195120
0.8564	High Similarity	NPC288759
0.8541	High Similarity	NPC298320
0.8488	Intermediate Similarity	NPC329830
0.8477	Intermediate Similarity	NPC301292
0.8477	Intermediate Similarity	NPC313112
0.8439	Intermediate Similarity	NPC118154
0.8439	Intermediate Similarity	NPC157983
0.841	Intermediate Similarity	NPC241263
0.7946	Intermediate Similarity	NPC204867
0.7917	Intermediate Similarity	NPC327005
0.7807	Intermediate Similarity	NPC299582
0.7757	Intermediate Similarity	NPC251071
0.7577	Intermediate Similarity	NPC9475
0.7463	Intermediate Similarity	NPC17677
0.7452	Intermediate Similarity	NPC41216
0.7436	Intermediate Similarity	NPC129578
0.7418	Intermediate Similarity	NPC470481
0.7418	Intermediate Similarity	NPC470482
0.7411	Intermediate Similarity	NPC98416
0.7379	Intermediate Similarity	NPC83019
0.7379	Intermediate Similarity	NPC112937
0.7376	Intermediate Similarity	NPC469437
0.7374	Intermediate Similarity	NPC309692
0.7368	Intermediate Similarity	NPC93653
0.7339	Intermediate Similarity	NPC469439
0.7337	Intermediate Similarity	NPC99723
0.733	Intermediate Similarity	NPC204580
0.7324	Intermediate Similarity	NPC25961
0.7313	Intermediate Similarity	NPC262725
0.7286	Intermediate Similarity	NPC472163
0.7277	Intermediate Similarity	NPC477825
0.7273	Intermediate Similarity	NPC471489
0.7273	Intermediate Similarity	NPC474815
0.7268	Intermediate Similarity	NPC471825
0.7268	Intermediate Similarity	NPC78284
0.7264	Intermediate Similarity	NPC478075
0.7256	Intermediate Similarity	NPC477826
0.7256	Intermediate Similarity	NPC477827
0.7245	Intermediate Similarity	NPC73280
0.7222	Intermediate Similarity	NPC127082
0.7219	Intermediate Similarity	NPC144691
0.7206	Intermediate Similarity	NPC208890
0.72	Intermediate Similarity	NPC227033
0.7196	Intermediate Similarity	NPC266499
0.7189	Intermediate Similarity	NPC52789
0.7189	Intermediate Similarity	NPC55832
0.7189	Intermediate Similarity	NPC268204
0.7189	Intermediate Similarity	NPC26051
0.7179	Intermediate Similarity	NPC317567
0.7174	Intermediate Similarity	NPC477956
0.717	Intermediate Similarity	NPC470484
0.7158	Intermediate Similarity	NPC472419
0.715	Intermediate Similarity	NPC85613
0.715	Intermediate Similarity	NPC100573
0.715	Intermediate Similarity	NPC330683
0.715	Intermediate Similarity	NPC207873
0.715	Intermediate Similarity	NPC264938
0.715	Intermediate Similarity	NPC329567
0.7143	Intermediate Similarity	NPC186397
0.7143	Intermediate Similarity	NPC37135
0.7136	Intermediate Similarity	NPC195787
0.7136	Intermediate Similarity	NPC246140
0.7135	Intermediate Similarity	NPC144118
0.7135	Intermediate Similarity	NPC80962
0.7135	Intermediate Similarity	NPC326109
0.7135	Intermediate Similarity	NPC259166
0.7135	Intermediate Similarity	NPC219917
0.7135	Intermediate Similarity	NPC253822
0.7135	Intermediate Similarity	NPC172250
0.7135	Intermediate Similarity	NPC48624
0.7135	Intermediate Similarity	NPC215311
0.7135	Intermediate Similarity	NPC101366
0.7135	Intermediate Similarity	NPC204985
0.7135	Intermediate Similarity	NPC213659
0.713	Intermediate Similarity	NPC220337
0.7123	Intermediate Similarity	NPC477828
0.712	Intermediate Similarity	NPC21350
0.7116	Intermediate Similarity	NPC46990
0.7113	Intermediate Similarity	NPC205255
0.7113	Intermediate Similarity	NPC119649
0.7113	Intermediate Similarity	NPC271388
0.7113	Intermediate Similarity	NPC230956
0.7113	Intermediate Similarity	NPC235143
0.7112	Intermediate Similarity	NPC18585
0.7112	Intermediate Similarity	NPC166138
0.7112	Intermediate Similarity	NPC106985
0.7105	Intermediate Similarity	NPC223988
0.7104	Intermediate Similarity	NPC477244
0.7104	Intermediate Similarity	NPC472364
0.7104	Intermediate Similarity	NPC186838
0.7104	Intermediate Similarity	NPC477242
0.7104	Intermediate Similarity	NPC150399
0.7104	Intermediate Similarity	NPC473391
0.7104	Intermediate Similarity	NPC477243
0.7104	Intermediate Similarity	NPC66349
0.7104	Intermediate Similarity	NPC12165
0.7104	Intermediate Similarity	NPC1486
0.7104	Intermediate Similarity	NPC168105
0.7104	Intermediate Similarity	NPC249606
0.7104	Intermediate Similarity	NPC274109
0.7104	Intermediate Similarity	NPC41461
0.7104	Intermediate Similarity	NPC25287
0.7104	Intermediate Similarity	NPC98115
0.7103	Intermediate Similarity	NPC308943
0.7097	Intermediate Similarity	NPC49108
0.7097	Intermediate Similarity	NPC469404
0.7089	Intermediate Similarity	NPC163829
0.7087	Intermediate Similarity	NPC151171
0.7085	Intermediate Similarity	NPC94842
0.7081	Intermediate Similarity	NPC283429
0.7081	Intermediate Similarity	NPC295384
0.7077	Intermediate Similarity	NPC80759
0.7077	Intermediate Similarity	NPC79402
0.7075	Intermediate Similarity	NPC1464
0.7074	Intermediate Similarity	NPC311741
0.7074	Intermediate Similarity	NPC476055
0.7074	Intermediate Similarity	NPC234629
0.7065	Intermediate Similarity	NPC153979
0.7065	Intermediate Similarity	NPC5167
0.7065	Intermediate Similarity	NPC317119
0.7062	Intermediate Similarity	NPC221864
0.7059	Intermediate Similarity	NPC144499
0.7056	Intermediate Similarity	NPC304837
0.7056	Intermediate Similarity	NPC158551
0.7056	Intermediate Similarity	NPC476258
0.7054	Intermediate Similarity	NPC122886
0.7053	Intermediate Similarity	NPC39195
0.7049	Intermediate Similarity	NPC156092
0.7049	Intermediate Similarity	NPC131039
0.7049	Intermediate Similarity	NPC13575
0.7048	Intermediate Similarity	NPC193906
0.7048	Intermediate Similarity	NPC23080
0.7043	Intermediate Similarity	NPC69769
0.7043	Intermediate Similarity	NPC11056
0.7037	Intermediate Similarity	NPC24136
0.7037	Intermediate Similarity	NPC290133
0.7037	Intermediate Similarity	NPC187282
0.7037	Intermediate Similarity	NPC477955
0.7037	Intermediate Similarity	NPC196114
0.7032	Intermediate Similarity	NPC298449
0.7027	Intermediate Similarity	NPC279668
0.7027	Intermediate Similarity	NPC90665
0.7027	Intermediate Similarity	NPC12175
0.7027	Intermediate Similarity	NPC309154
0.7027	Intermediate Similarity	NPC278323
0.7027	Intermediate Similarity	NPC55162
0.7027	Intermediate Similarity	NPC243528
0.7027	Intermediate Similarity	NPC251681
0.7024	Intermediate Similarity	NPC18306
0.7021	Intermediate Similarity	NPC149026
0.7021	Intermediate Similarity	NPC476178
0.7021	Intermediate Similarity	NPC221432
0.7021	Intermediate Similarity	NPC150408
0.7021	Intermediate Similarity	NPC39329
0.7021	Intermediate Similarity	NPC164980
0.7021	Intermediate Similarity	NPC143896
0.7021	Intermediate Similarity	NPC117836
0.7021	Intermediate Similarity	NPC51887
0.7021	Intermediate Similarity	NPC175504
0.7021	Intermediate Similarity	NPC91560
0.7021	Intermediate Similarity	NPC75049
0.7021	Intermediate Similarity	NPC310130
0.7021	Intermediate Similarity	NPC475705
0.7021	Intermediate Similarity	NPC257097
0.7021	Intermediate Similarity	NPC68104
0.7021	Intermediate Similarity	NPC169591
0.7018	Intermediate Similarity	NPC476429
0.7016	Intermediate Similarity	NPC65775
0.7016	Intermediate Similarity	NPC38545

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 NPC212123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	702
0.2-0.3	1030
0.3-0.4	1693
0.4-0.5	2746
0.5-0.6	2032
0.6-0.7	569
0.7-0.8	65
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
0.904	High Similarity	NPD2899	Discontinued
0.7535	Intermediate Similarity	NPD5496	Approved
0.7524	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD6874	Approved
0.75	Intermediate Similarity	NPD3298	Approved
0.7488	Intermediate Similarity	NPD5860	Discontinued
0.7488	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD8461	Discontinued
0.7403	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6104	Discontinued
0.7366	Intermediate Similarity	NPD6625	Approved
0.7343	Intermediate Similarity	NPD3297	Approved
0.7339	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1945	Phase 1
0.7251	Intermediate Similarity	NPD4456	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6795	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5183	Approved
0.7231	Intermediate Similarity	NPD5186	Approved
0.723	Intermediate Similarity	NPD4082	Approved
0.722	Intermediate Similarity	NPD5937	Approved
0.7204	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8067	Phase 3
0.7188	Intermediate Similarity	NPD7654	Discontinued
0.7183	Intermediate Similarity	NPD4596	Phase 1
0.7179	Intermediate Similarity	NPD8367	Approved
0.715	Intermediate Similarity	NPD4360	Phase 2
0.715	Intermediate Similarity	NPD4022	Approved
0.715	Intermediate Similarity	NPD3472	Approved
0.715	Intermediate Similarity	NPD2906	Approved
0.715	Intermediate Similarity	NPD2907	Approved
0.715	Intermediate Similarity	NPD4363	Phase 3
0.7131	Intermediate Similarity	NPD8492	Approved
0.7115	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4361	Phase 2
0.7104	Intermediate Similarity	NPD3783	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6198	Phase 1
0.7089	Intermediate Similarity	NPD4465	Phase 2
0.7089	Intermediate Similarity	NPD4467	Phase 2
0.7083	Intermediate Similarity	NPD3372	Discontinued
0.7061	Intermediate Similarity	NPD7922	Phase 1
0.705	Intermediate Similarity	NPD3793	Phase 3
0.705	Intermediate Similarity	NPD6020	Phase 2
0.7023	Intermediate Similarity	NPD7584	Approved
0.702	Intermediate Similarity	NPD5242	Approved
0.7018	Intermediate Similarity	NPD4494	Approved
0.7018	Intermediate Similarity	NPD4492	Approved
0.7004	Intermediate Similarity	NPD4981	Phase 2
0.7	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD1483	Discontinued
0.6995	Remote Similarity	NPD5006	Approved
0.6995	Remote Similarity	NPD5005	Approved
0.6995	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5711	Approved
0.697	Remote Similarity	NPD5710	Approved
0.6967	Remote Similarity	NPD5197	Approved
0.6967	Remote Similarity	NPD5196	Approved
0.6967	Remote Similarity	NPD5194	Approved
0.695	Remote Similarity	NPD3446	Phase 1
0.6942	Remote Similarity	NPD4515	Suspended
0.693	Remote Similarity	NPD6199	Discontinued
0.6923	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1898	Discontinued
0.6897	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4493	Discontinued
0.6892	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4668	Phase 2
0.6872	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD1510	Phase 2
0.6857	Remote Similarity	NPD4539	Phase 1
0.6849	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3893	Discontinued
0.6847	Remote Similarity	NPD7479	Phase 2
0.6842	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7585	Approved
0.6835	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD2821	Approved
0.6832	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1240	Approved
0.6828	Remote Similarity	NPD3925	Approved
0.6824	Remote Similarity	NPD4846	Phase 2
0.6818	Remote Similarity	NPD683	Approved
0.6814	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2654	Approved
0.6808	Remote Similarity	NPD4420	Approved
0.6808	Remote Similarity	NPD5071	Phase 2
0.6804	Remote Similarity	NPD4380	Phase 2
0.6789	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7583	Approved
0.6789	Remote Similarity	NPD7263	Phase 2
0.6787	Remote Similarity	NPD3888	Discontinued
0.6786	Remote Similarity	NPD7819	Suspended
0.6774	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5488	Discontinued
0.6758	Remote Similarity	NPD7701	Phase 2
0.6757	Remote Similarity	NPD1607	Approved
0.6757	Remote Similarity	NPD4455	Discontinued
0.6755	Remote Similarity	NPD1549	Phase 2
0.6749	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2339	Phase 3
0.6737	Remote Similarity	NPD6790	Phase 1
0.6737	Remote Similarity	NPD7417	Discontinued
0.6735	Remote Similarity	NPD6844	Discontinued
0.6733	Remote Similarity	NPD2246	Approved
0.6733	Remote Similarity	NPD2248	Approved
0.6726	Remote Similarity	NPD3437	Discontinued
0.6719	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5928	Phase 1
0.6713	Remote Similarity	NPD6321	Discontinued
0.6712	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1926	Approved
0.6711	Remote Similarity	NPD7279	Phase 2
0.6711	Remote Similarity	NPD7278	Phase 2
0.6702	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5637	Discontinued
0.6696	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5890	Approved
0.6684	Remote Similarity	NPD7411	Suspended
0.6684	Remote Similarity	NPD5889	Approved
0.6683	Remote Similarity	NPD955	Approved
0.6683	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7075	Discontinued
0.6682	Remote Similarity	NPD5195	Discontinued
0.6681	Remote Similarity	NPD2300	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5978	Approved
0.6667	Remote Similarity	NPD5977	Approved
0.6652	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1220	Phase 1
0.665	Remote Similarity	NPD1934	Approved
0.6638	Remote Similarity	NPD3912	Discontinued
0.6637	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7043	Discontinued
0.6635	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD1221	Approved
0.6633	Remote Similarity	NPD6585	Discontinued
0.6627	Remote Similarity	NPD7803	Approved
0.6623	Remote Similarity	NPD7907	Approved
0.6623	Remote Similarity	NPD3259	Approved
0.6622	Remote Similarity	NPD8149	Discontinued
0.6621	Remote Similarity	NPD6644	Discontinued
0.662	Remote Similarity	NPD5609	Approved
0.662	Remote Similarity	NPD5610	Approved
0.662	Remote Similarity	NPD5608	Approved
0.6619	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD2801	Approved
0.6616	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1505	Phase 2
0.6603	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2247	Approved
0.6584	Remote Similarity	NPD2249	Approved
0.658	Remote Similarity	NPD3263	Phase 3
0.6562	Remote Similarity	NPD7301	Phase 3
0.6561	Remote Similarity	NPD2935	Discontinued
0.6561	Remote Similarity	NPD2796	Approved
0.656	Remote Similarity	NPD2493	Approved
0.656	Remote Similarity	NPD2494	Approved
0.656	Remote Similarity	NPD3450	Approved
0.656	Remote Similarity	NPD3452	Approved
0.6555	Remote Similarity	NPD7546	Discontinued
0.6555	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6232	Discontinued
0.655	Remote Similarity	NPD3882	Suspended
0.6548	Remote Similarity	NPD5617	Suspended
0.6547	Remote Similarity	NPD5914	Approved
0.6545	Remote Similarity	NPD1294	Discontinued
0.6544	Remote Similarity	NPD8285	Discontinued
0.6544	Remote Similarity	NPD7811	Phase 3
0.6544	Remote Similarity	NPD7810	Phase 3
0.6543	Remote Similarity	NPD3986	Discontinued
0.6538	Remote Similarity	NPD6962	Phase 2
0.6537	Remote Similarity	NPD7473	Discontinued
0.6535	Remote Similarity	NPD4665	Approved
0.6535	Remote Similarity	NPD4111	Phase 1
0.6533	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.653	Remote Similarity	NPD7626	Approved
0.653	Remote Similarity	NPD7627	Approved
0.6528	Remote Similarity	NPD2975	Approved
0.6528	Remote Similarity	NPD4605	Approved
0.6528	Remote Similarity	NPD2974	Approved
0.6528	Remote Similarity	NPD2973	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