NPASS Compound

Structure

CID148391 OpenBabel06191715522D 22 24 0 0 0 0 0 0 0 0999 V2000 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 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 -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 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 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 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 16 2 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 20 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.1
Volume:	296.116
LogP:	2.271
LogD:	2.273
LogS:	-3.843
# Rotatable Bonds:	2
TPSA:	80.92
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	2.562
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.904
MDCK Permeability:	1.5721780073363334e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	92.15259552001953%
Volume Distribution (VD):	0.703
Pgp-substrate:	7.4816389083862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.24
CYP2C19-substrate:	0.476
CYP2C9-inhibitor:	0.611
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.418
CYP2D6-substrate:	0.675
CYP3A4-inhibitor:	0.401
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	5.237
Half-life (T1/2):	0.493

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.556
AMES Toxicity:	0.779
Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.847
Skin Sensitization:	0.424
Carcinogencity:	0.815
Eye Corrosion:	0.023
Eye Irritation:	0.938
Respiratory Toxicity:	0.566

Download Data

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

Natural Product: NPC148391

Natural Product ID:	NPC148391
*Common Name:**	Citrusinine-I
IUPAC Name:	1,5-dihydroxy-3,4-dimethoxy-10-methylacridin-9-one
Synonyms:	Citrusinine-I
Standard InCHIKey:	UTEAJHNFBCLZHN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H15NO5/c1-17-13-8(5-4-6-9(13)18)15(20)12-10(19)7-11(21-2)16(22-3)14(12)17/h4-7,18-19H,1-3H3
SMILES:	Cn1c2c(cccc2O)c(=O)c2c(cc(c(c12)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451705
PubChem CID:	5487772
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
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO33332	severinia buxifolia	Species	Rutaceae	Eukaryota	root bark	Hainan	n.a.	PMID[11520222]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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]
NPO19787	Citrus sinensis	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
NPO19787	NPC148391	Raw	Root Bark	8	8	8	mg/100g	Database [DUKE]

☑ 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
ED50	3
IC50	5
Ki	1

Activity Type	# Activity
Cell Line	6
Individual Protein	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	ED50	=	6.3	ug ml-1	PMID[516327]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.09	ug ml-1	PMID[516327]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[516328]
NPT319	Cell Line	B16	Mus musculus	IC50	>	40000.0	nM	PMID[516328]
NPT1353	Cell Line	CCRF-HSB-2	Homo sapiens	IC50	>	40000.0	nM	PMID[516328]
NPT1354	Cell Line	TGBC11TKB	Homo sapiens	IC50	>	40000.0	nM	PMID[516328]
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	IC50	=	2200.0	nM	PMID[516329]
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	Ki	=	1000.0	nM	PMID[516329]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	6.6	ug ml-1	PMID[516327]

☑ 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 NPC148391 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	600
0.1-0.2	3385
0.2-0.3	11934
0.3-0.4	4974
0.4-0.5	8646
0.5-0.6	10512
0.6-0.7	2378
0.7-0.8	212
0.8-0.85	23
0.85-0.9	14
0.9-0.95	12
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC2905
0.9742	High Similarity	NPC134702
0.974	High Similarity	NPC114468
0.9694	High Similarity	NPC76478
0.9594	High Similarity	NPC7560
0.9495	High Similarity	NPC118189
0.9453	High Similarity	NPC13249
0.9442	High Similarity	NPC182853
0.9337	High Similarity	NPC268223
0.9326	High Similarity	NPC212123
0.9307	High Similarity	NPC285254
0.9137	High Similarity	NPC295479
0.9137	High Similarity	NPC220241
0.9059	High Similarity	NPC157983
0.9059	High Similarity	NPC118154
0.9045	High Similarity	NPC30749
0.8995	High Similarity	NPC305542
0.896	High Similarity	NPC195120
0.8894	High Similarity	NPC474366
0.8867	High Similarity	NPC87560
0.8808	High Similarity	NPC170333
0.8756	High Similarity	NPC218303
0.875	High Similarity	NPC114039
0.875	High Similarity	NPC206109
0.8627	High Similarity	NPC176113
0.8439	Intermediate Similarity	NPC116178
0.8398	Intermediate Similarity	NPC321166
0.8398	Intermediate Similarity	NPC217903
0.8374	Intermediate Similarity	NPC198160
0.8366	Intermediate Similarity	NPC133156
0.8358	Intermediate Similarity	NPC15987
0.8229	Intermediate Similarity	NPC298320
0.8223	Intermediate Similarity	NPC1820
0.8159	Intermediate Similarity	NPC234933
0.8122	Intermediate Similarity	NPC329830
0.8088	Intermediate Similarity	NPC288759
0.7923	Intermediate Similarity	NPC301292
0.7923	Intermediate Similarity	NPC313112
0.7854	Intermediate Similarity	NPC241263
0.7773	Intermediate Similarity	NPC477825
0.7766	Intermediate Similarity	NPC98416
0.7664	Intermediate Similarity	NPC477827
0.7664	Intermediate Similarity	NPC477826
0.7656	Intermediate Similarity	NPC204867
0.7581	Intermediate Similarity	NPC470481
0.7581	Intermediate Similarity	NPC470482
0.7548	Intermediate Similarity	NPC83019
0.7526	Intermediate Similarity	NPC299582
0.7523	Intermediate Similarity	NPC477828
0.75	Intermediate Similarity	NPC204580
0.7464	Intermediate Similarity	NPC17677
0.7425	Intermediate Similarity	NPC107123
0.7404	Intermediate Similarity	NPC134637
0.7404	Intermediate Similarity	NPC203373
0.7379	Intermediate Similarity	NPC208890
0.7376	Intermediate Similarity	NPC327005
0.7356	Intermediate Similarity	NPC78284
0.7354	Intermediate Similarity	NPC251071
0.7344	Intermediate Similarity	NPC156953
0.7327	Intermediate Similarity	NPC85613
0.7327	Intermediate Similarity	NPC5167
0.7324	Intermediate Similarity	NPC2173
0.7324	Intermediate Similarity	NPC202771
0.7324	Intermediate Similarity	NPC328700
0.7324	Intermediate Similarity	NPC119818
0.7317	Intermediate Similarity	NPC262725
0.7313	Intermediate Similarity	NPC9475
0.7306	Intermediate Similarity	NPC117579
0.7306	Intermediate Similarity	NPC149614
0.7306	Intermediate Similarity	NPC262623
0.7284	Intermediate Similarity	NPC304837
0.7284	Intermediate Similarity	NPC476258
0.7282	Intermediate Similarity	NPC18306
0.7277	Intermediate Similarity	NPC471489
0.7277	Intermediate Similarity	NPC119660
0.7277	Intermediate Similarity	NPC93034
0.7268	Intermediate Similarity	NPC131266
0.7268	Intermediate Similarity	NPC216769
0.7268	Intermediate Similarity	NPC209487
0.7268	Intermediate Similarity	NPC35763
0.7268	Intermediate Similarity	NPC245382
0.7268	Intermediate Similarity	NPC291802
0.7268	Intermediate Similarity	NPC269451
0.7268	Intermediate Similarity	NPC100263
0.7268	Intermediate Similarity	NPC181209
0.7268	Intermediate Similarity	NPC100971
0.7268	Intermediate Similarity	NPC121522
0.7265	Intermediate Similarity	NPC160100
0.7256	Intermediate Similarity	NPC163829
0.7254	Intermediate Similarity	NPC239363
0.7254	Intermediate Similarity	NPC179183
0.7253	Intermediate Similarity	NPC119134
0.725	Intermediate Similarity	NPC73280
0.7249	Intermediate Similarity	NPC476429
0.7243	Intermediate Similarity	NPC66815
0.724	Intermediate Similarity	NPC287395
0.724	Intermediate Similarity	NPC183655
0.7235	Intermediate Similarity	NPC207873
0.7235	Intermediate Similarity	NPC100573
0.7231	Intermediate Similarity	NPC271779
0.7231	Intermediate Similarity	NPC472915
0.7231	Intermediate Similarity	NPC167091
0.7231	Intermediate Similarity	NPC124714
0.7231	Intermediate Similarity	NPC206238
0.7231	Intermediate Similarity	NPC292214
0.7231	Intermediate Similarity	NPC88645
0.7222	Intermediate Similarity	NPC113455
0.7222	Intermediate Similarity	NPC158551
0.7222	Intermediate Similarity	NPC477395
0.7217	Intermediate Similarity	NPC112937
0.7216	Intermediate Similarity	NPC19980
0.7216	Intermediate Similarity	NPC45291
0.7208	Intermediate Similarity	NPC99597
0.7208	Intermediate Similarity	NPC210084
0.7208	Intermediate Similarity	NPC181960
0.7206	Intermediate Similarity	NPC329816
0.7202	Intermediate Similarity	NPC102003
0.7202	Intermediate Similarity	NPC92722
0.7194	Intermediate Similarity	NPC2928
0.7194	Intermediate Similarity	NPC39184
0.7194	Intermediate Similarity	NPC472909
0.7194	Intermediate Similarity	NPC37392
0.7193	Intermediate Similarity	NPC315914
0.7192	Intermediate Similarity	NPC474815
0.7192	Intermediate Similarity	NPC287152
0.719	Intermediate Similarity	NPC254957
0.7189	Intermediate Similarity	NPC308943
0.7179	Intermediate Similarity	NPC199100
0.7179	Intermediate Similarity	NPC39007
0.7179	Intermediate Similarity	NPC180234
0.7179	Intermediate Similarity	NPC120537
0.7179	Intermediate Similarity	NPC101996
0.7179	Intermediate Similarity	NPC161277
0.7178	Intermediate Similarity	NPC120513
0.7176	Intermediate Similarity	NPC268077
0.7168	Intermediate Similarity	NPC94842
0.7165	Intermediate Similarity	NPC306821
0.7165	Intermediate Similarity	NPC10467
0.7163	Intermediate Similarity	NPC286135
0.7157	Intermediate Similarity	NPC472916
0.7157	Intermediate Similarity	NPC255106
0.7157	Intermediate Similarity	NPC235165
0.7155	Intermediate Similarity	NPC302807
0.715	Intermediate Similarity	NPC131451
0.715	Intermediate Similarity	NPC15329
0.7143	Intermediate Similarity	NPC280937
0.7143	Intermediate Similarity	NPC250557
0.7143	Intermediate Similarity	NPC226708
0.7136	Intermediate Similarity	NPC71124
0.7136	Intermediate Similarity	NPC215098
0.7136	Intermediate Similarity	NPC124302
0.7136	Intermediate Similarity	NPC70290
0.7136	Intermediate Similarity	NPC73020
0.7136	Intermediate Similarity	NPC14622
0.7136	Intermediate Similarity	NPC46744
0.7136	Intermediate Similarity	NPC473562
0.7135	Intermediate Similarity	NPC12377
0.7131	Intermediate Similarity	NPC58209
0.7131	Intermediate Similarity	NPC120239
0.713	Intermediate Similarity	NPC41216
0.7128	Intermediate Similarity	NPC226973
0.7128	Intermediate Similarity	NPC251110
0.7128	Intermediate Similarity	NPC208043
0.7128	Intermediate Similarity	NPC308451
0.7128	Intermediate Similarity	NPC171010
0.7124	Intermediate Similarity	NPC148124
0.7123	Intermediate Similarity	NPC46990
0.7121	Intermediate Similarity	NPC78225
0.7121	Intermediate Similarity	NPC472913
0.7121	Intermediate Similarity	NPC262286
0.7121	Intermediate Similarity	NPC162869
0.7121	Intermediate Similarity	NPC472910
0.7121	Intermediate Similarity	NPC222814
0.7121	Intermediate Similarity	NPC245758
0.7121	Intermediate Similarity	NPC474208
0.7121	Intermediate Similarity	NPC475267
0.7121	Intermediate Similarity	NPC472911
0.7121	Intermediate Similarity	NPC96167
0.7121	Intermediate Similarity	NPC36852
0.7121	Intermediate Similarity	NPC156057
0.7121	Intermediate Similarity	NPC476981
0.7121	Intermediate Similarity	NPC48208
0.7121	Intermediate Similarity	NPC472914
0.7121	Intermediate Similarity	NPC474836
0.7117	Intermediate Similarity	NPC298449
0.7113	Intermediate Similarity	NPC195763
0.7113	Intermediate Similarity	NPC142876
0.7113	Intermediate Similarity	NPC139293
0.7113	Intermediate Similarity	NPC40290
0.7113	Intermediate Similarity	NPC264550
0.7113	Intermediate Similarity	NPC333691
0.7113	Intermediate Similarity	NPC69430
0.7113	Intermediate Similarity	NPC264289
0.7113	Intermediate Similarity	NPC200060
0.7112	Intermediate Similarity	NPC160113
0.7112	Intermediate Similarity	NPC34770
0.7112	Intermediate Similarity	NPC476220
0.711	Intermediate Similarity	NPC16249
0.7107	Intermediate Similarity	NPC31018
0.7107	Intermediate Similarity	NPC130589

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 NPC148391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	723
0.2-0.3	1129
0.3-0.4	1952
0.4-0.5	2673
0.5-0.6	1820
0.6-0.7	461
0.7-0.8	49
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9592	High Similarity	NPD2899	Discontinued
0.7679	Intermediate Similarity	NPD6625	Approved
0.75	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5242	Approved
0.7348	Intermediate Similarity	NPD4846	Phase 2
0.7324	Intermediate Similarity	NPD5005	Approved
0.7324	Intermediate Similarity	NPD5006	Approved
0.7296	Intermediate Similarity	NPD1483	Discontinued
0.7257	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5860	Discontinued
0.7188	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6874	Approved
0.7176	Intermediate Similarity	NPD3298	Approved
0.7163	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD8461	Discontinued
0.7143	Intermediate Similarity	NPD7922	Phase 1
0.7136	Intermediate Similarity	NPD4420	Approved
0.7136	Intermediate Similarity	NPD1945	Phase 1
0.713	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6104	Discontinued
0.7116	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3297	Approved
0.7067	Intermediate Similarity	NPD5496	Approved
0.7059	Intermediate Similarity	NPD683	Approved
0.7056	Intermediate Similarity	NPD2801	Approved
0.7032	Intermediate Similarity	NPD7263	Phase 2
0.7018	Intermediate Similarity	NPD4456	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5102	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2821	Approved
0.7005	Intermediate Similarity	NPD1934	Approved
0.7005	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4082	Approved
0.6983	Remote Similarity	NPD8067	Phase 3
0.6977	Remote Similarity	NPD5071	Phase 2
0.6971	Remote Similarity	NPD8367	Approved
0.697	Remote Similarity	NPD7654	Discontinued
0.696	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD4596	Phase 1
0.6927	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD8492	Approved
0.6923	Remote Similarity	NPD2906	Approved
0.6923	Remote Similarity	NPD3472	Approved
0.6923	Remote Similarity	NPD2907	Approved
0.6923	Remote Similarity	NPD4022	Approved
0.6897	Remote Similarity	NPD5183	Approved
0.6897	Remote Similarity	NPD5186	Approved
0.6895	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7224	Discontinued
0.6883	Remote Similarity	NPD7223	Discontinued
0.6864	Remote Similarity	NPD4467	Phase 2
0.6864	Remote Similarity	NPD4465	Phase 2
0.6861	Remote Similarity	NPD3372	Discontinued
0.6861	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7907	Approved
0.6853	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5353	Approved
0.685	Remote Similarity	NPD5977	Approved
0.685	Remote Similarity	NPD5978	Approved
0.6835	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2339	Phase 3
0.682	Remote Similarity	NPD5197	Approved
0.682	Remote Similarity	NPD5194	Approved
0.682	Remote Similarity	NPD5196	Approved
0.6802	Remote Similarity	NPD7584	Approved
0.68	Remote Similarity	NPD4494	Approved
0.68	Remote Similarity	NPD4492	Approved
0.68	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6198	Phase 1
0.6797	Remote Similarity	NPD7278	Phase 2
0.6797	Remote Similarity	NPD7279	Phase 2
0.6773	Remote Similarity	NPD7803	Approved
0.6771	Remote Similarity	NPD7701	Phase 2
0.6771	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4665	Approved
0.6769	Remote Similarity	NPD4111	Phase 1
0.6762	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1898	Discontinued
0.6759	Remote Similarity	NPD4363	Phase 3
0.6759	Remote Similarity	NPD4360	Phase 2
0.6748	Remote Similarity	NPD1220	Phase 1
0.6746	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5937	Approved
0.6733	Remote Similarity	NPD3882	Suspended
0.6731	Remote Similarity	NPD3793	Phase 3
0.6731	Remote Similarity	NPD1221	Approved
0.6727	Remote Similarity	NPD2493	Approved
0.6727	Remote Similarity	NPD3452	Approved
0.6727	Remote Similarity	NPD3450	Approved
0.6727	Remote Similarity	NPD2494	Approved
0.6723	Remote Similarity	NPD6199	Discontinued
0.6716	Remote Similarity	NPD5494	Approved
0.6714	Remote Similarity	NPD4515	Suspended
0.6711	Remote Similarity	NPD5914	Approved
0.6711	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6386	Approved
0.67	Remote Similarity	NPD6385	Approved
0.6697	Remote Similarity	NPD2973	Approved
0.6697	Remote Similarity	NPD4605	Approved
0.6697	Remote Similarity	NPD2974	Approved
0.6697	Remote Similarity	NPD4604	Approved
0.6697	Remote Similarity	NPD2975	Approved
0.6696	Remote Similarity	NPD7585	Approved
0.6695	Remote Similarity	NPD7048	Phase 3
0.6695	Remote Similarity	NPD1505	Phase 2
0.6684	Remote Similarity	NPD1511	Approved
0.6683	Remote Similarity	NPD824	Approved
0.6682	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6997	Phase 2
0.6681	Remote Similarity	NPD4493	Discontinued
0.6681	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4668	Phase 2
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD6844	Discontinued
0.6653	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7583	Approved
0.6651	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4361	Phase 2
0.6651	Remote Similarity	NPD5582	Discontinued
0.6651	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5710	Approved
0.665	Remote Similarity	NPD6232	Discontinued
0.665	Remote Similarity	NPD5711	Approved
0.6639	Remote Similarity	NPD7886	Phase 2
0.6639	Remote Similarity	NPD7885	Phase 2
0.6638	Remote Similarity	NPD8149	Discontinued
0.6638	Remote Similarity	NPD7805	Phase 3
0.6638	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6644	Discontinued
0.6637	Remote Similarity	NPD3893	Discontinued
0.6637	Remote Similarity	NPD4583	Approved
0.6637	Remote Similarity	NPD4582	Approved
0.6636	Remote Similarity	NPD7125	Discontinued
0.6635	Remote Similarity	NPD7473	Discontinued
0.6634	Remote Similarity	NPD5677	Discontinued
0.6621	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.662	Remote Similarity	NPD8054	Approved
0.662	Remote Similarity	NPD8053	Approved
0.6616	Remote Similarity	NPD1512	Approved
0.6615	Remote Similarity	NPD1510	Phase 2
0.6614	Remote Similarity	NPD7708	Approved
0.6606	Remote Similarity	NPD4580	Approved
0.6603	Remote Similarity	NPD3818	Discontinued
0.66	Remote Similarity	NPD8091	Phase 3
0.6595	Remote Similarity	NPD3437	Discontinued
0.6594	Remote Similarity	NPD7559	Phase 2
0.6592	Remote Similarity	NPD4004	Approved
0.6592	Remote Similarity	NPD4002	Approved
0.6588	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4981	Phase 2
0.6579	Remote Similarity	NPD7225	Discontinued
0.6579	Remote Similarity	NPD3888	Discontinued
0.6579	Remote Similarity	NPD1240	Approved
0.6578	Remote Similarity	NPD7043	Discontinued
0.6574	Remote Similarity	NPD7956	Approved
0.6574	Remote Similarity	NPD2843	Phase 2
0.6574	Remote Similarity	NPD2845	Phase 2
0.6574	Remote Similarity	NPD7955	Approved
0.6574	Remote Similarity	NPD5928	Phase 1
0.6571	Remote Similarity	NPD6020	Phase 2
0.6569	Remote Similarity	NPD6788	Approved
0.6567	Remote Similarity	NPD4380	Phase 2
0.6561	Remote Similarity	NPD5609	Approved
0.6561	Remote Similarity	NPD5608	Approved
0.656	Remote Similarity	NPD4539	Phase 1
0.6557	Remote Similarity	NPD7039	Approved
0.6557	Remote Similarity	NPD7038	Approved
0.6556	Remote Similarity	NPD2300	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD3446	Phase 1
0.6553	Remote Similarity	NPD3925	Approved
0.6552	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.655	Remote Similarity	NPD4455	Discontinued
0.6545	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5195	Discontinued
0.6544	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7417	Discontinued
0.654	Remote Similarity	NPD7074	Phase 3
0.6526	Remote Similarity	NPD7549	Discontinued
0.6526	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.652	Remote Similarity	NPD3817	Phase 2
0.6513	Remote Similarity	NPD1549	Phase 2
0.6511	Remote Similarity	NPD3912	Discontinued
0.651	Remote Similarity	NPD1607	Approved
0.6507	Remote Similarity	NPD2248	Approved
0.6507	Remote Similarity	NPD2246	Approved
0.6502	Remote Similarity	NPD6321	Discontinued
0.65	Remote Similarity	NPD3640	Phase 3
0.65	Remote Similarity	NPD3641	Approved
0.65	Remote Similarity	NPD3639	Approved
0.6498	Remote Similarity	NPD6377	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