NPASS Compound

Structure

NPC1820 OpenBabel07101718182D 23 25 0 0 0 0 0 0 0 0999 V2000 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 2.5981 -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 1.7321 -1.0000 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 -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 -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 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 N 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 -3.4641 2.0000 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 4 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 20 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 13 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 17 2 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	309.14
Volume:	327.787
LogP:	3.44
LogD:	3.088
LogS:	-4.082
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	2.125
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.712
MDCK Permeability:	2.2020556571078487e-05
Pgp-inhibitor:	0.689
Pgp-substrate:	0.074
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.099

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.885
Plasma Protein Binding (PPB):	89.82242584228516%
Volume Distribution (VD):	1.066
Pgp-substrate:	3.350015640258789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.934
CYP2C19-substrate:	0.141
CYP2C9-inhibitor:	0.844
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.461
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	4.109
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.171
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.567
AMES Toxicity:	0.895
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.765
Skin Sensitization:	0.451
Carcinogencity:	0.709
Eye Corrosion:	0.008
Eye Irritation:	0.436
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC1820

Natural Product ID:	NPC1820
*Common Name:**	Crataemine
IUPAC Name:	1-ethyl-5,7-dimethoxy-3-phenylquinolin-4-one
Synonyms:	crataemine
Standard InCHIKey:	YFRCEQSYANGNOV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19NO3/c1-4-20-12-15(13-8-6-5-7-9-13)19(21)18-16(20)10-14(22-2)11-17(18)23-3/h5-12H,4H2,1-3H3
SMILES:	CCn1cc(c2ccccc2)c(=O)c2c1cc(cc2OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2322187
PubChem CID:	71574100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002348] Phenylquinolines

*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
NPO32925	crataeva nurvala	Species	Capparaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[23354071]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	76.8	%	PMID[566429]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	17.2	%	PMID[566429]

☑ 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 NPC1820 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	563
0.1-0.2	3436
0.2-0.3	12682
0.3-0.4	4087
0.4-0.5	10366
0.5-0.6	9394
0.6-0.7	1714
0.7-0.8	395
0.8-0.85	45
0.85-0.9	11
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9218	High Similarity	NPC234933
0.9153	High Similarity	NPC206109
0.9153	High Similarity	NPC114039
0.8913	High Similarity	NPC15987
0.8876	High Similarity	NPC299582
0.8852	High Similarity	NPC241263
0.8824	High Similarity	NPC198160
0.8624	High Similarity	NPC212123
0.8594	High Similarity	NPC116178
0.8588	High Similarity	NPC298320
0.8549	High Similarity	NPC217903
0.8549	High Similarity	NPC321166
0.8542	High Similarity	NPC220241
0.8542	High Similarity	NPC295479
0.8511	High Similarity	NPC288759
0.8454	Intermediate Similarity	NPC268223
0.8454	Intermediate Similarity	NPC30749
0.8421	Intermediate Similarity	NPC313112
0.8421	Intermediate Similarity	NPC301292
0.8402	Intermediate Similarity	NPC305542
0.8283	Intermediate Similarity	NPC195120
0.8283	Intermediate Similarity	NPC182853
0.8283	Intermediate Similarity	NPC87560
0.8283	Intermediate Similarity	NPC134702
0.825	Intermediate Similarity	NPC329830
0.8223	Intermediate Similarity	NPC148391
0.8205	Intermediate Similarity	NPC474366
0.8159	Intermediate Similarity	NPC118189
0.8109	Intermediate Similarity	NPC157983
0.8109	Intermediate Similarity	NPC118154
0.8095	Intermediate Similarity	NPC170333
0.8081	Intermediate Similarity	NPC114468
0.8071	Intermediate Similarity	NPC218303
0.8069	Intermediate Similarity	NPC76478
0.8057	Intermediate Similarity	NPC93653
0.804	Intermediate Similarity	NPC176113
0.804	Intermediate Similarity	NPC2905
0.798	Intermediate Similarity	NPC7560
0.7966	Intermediate Similarity	NPC204867
0.7961	Intermediate Similarity	NPC13249
0.7897	Intermediate Similarity	NPC41216
0.7895	Intermediate Similarity	NPC471825
0.788	Intermediate Similarity	NPC85613
0.7857	Intermediate Similarity	NPC133156
0.7784	Intermediate Similarity	NPC5167
0.7772	Intermediate Similarity	NPC9475
0.7742	Intermediate Similarity	NPC327005
0.774	Intermediate Similarity	NPC285254
0.7701	Intermediate Similarity	NPC144691
0.75	Intermediate Similarity	NPC283810
0.7423	Intermediate Similarity	NPC22476
0.7419	Intermediate Similarity	NPC73280
0.7413	Intermediate Similarity	NPC87714
0.7402	Intermediate Similarity	NPC25961
0.7376	Intermediate Similarity	NPC477161
0.7374	Intermediate Similarity	NPC100863
0.731	Intermediate Similarity	NPC223354
0.7306	Intermediate Similarity	NPC151171
0.7286	Intermediate Similarity	NPC71124
0.7282	Intermediate Similarity	NPC45389
0.7282	Intermediate Similarity	NPC474059
0.7282	Intermediate Similarity	NPC208890
0.7277	Intermediate Similarity	NPC115588
0.7277	Intermediate Similarity	NPC472163
0.7273	Intermediate Similarity	NPC471604
0.7251	Intermediate Similarity	NPC182428
0.7247	Intermediate Similarity	NPC242000
0.7241	Intermediate Similarity	NPC268077
0.7235	Intermediate Similarity	NPC476429
0.7209	Intermediate Similarity	NPC292998
0.7208	Intermediate Similarity	NPC473004
0.7194	Intermediate Similarity	NPC473569
0.7184	Intermediate Similarity	NPC254741
0.7172	Intermediate Similarity	NPC254957
0.7171	Intermediate Similarity	NPC16249
0.717	Intermediate Similarity	NPC469439
0.7164	Intermediate Similarity	NPC5374
0.7159	Intermediate Similarity	NPC308197
0.7158	Intermediate Similarity	NPC472894
0.7128	Intermediate Similarity	NPC150308
0.712	Intermediate Similarity	NPC127082
0.7118	Intermediate Similarity	NPC211120
0.7115	Intermediate Similarity	NPC146418
0.7108	Intermediate Similarity	NPC207971
0.7098	Intermediate Similarity	NPC28368
0.7094	Intermediate Similarity	NPC232600
0.7093	Intermediate Similarity	NPC284424
0.7087	Intermediate Similarity	NPC478075
0.7087	Intermediate Similarity	NPC308943
0.7083	Intermediate Similarity	NPC476436
0.7077	Intermediate Similarity	NPC49184
0.7077	Intermediate Similarity	NPC473007
0.7068	Intermediate Similarity	NPC129578
0.7062	Intermediate Similarity	NPC99723
0.7059	Intermediate Similarity	NPC153631
0.7053	Intermediate Similarity	NPC307640
0.7052	Intermediate Similarity	NPC473655
0.7052	Intermediate Similarity	NPC101294
0.705	Intermediate Similarity	NPC230313
0.7045	Intermediate Similarity	NPC7013
0.7045	Intermediate Similarity	NPC162680
0.7045	Intermediate Similarity	NPC294409
0.7045	Intermediate Similarity	NPC116632
0.7045	Intermediate Similarity	NPC303644
0.7045	Intermediate Similarity	NPC209560
0.7045	Intermediate Similarity	NPC181124
0.7043	Intermediate Similarity	NPC199737
0.7037	Intermediate Similarity	NPC122886
0.703	Intermediate Similarity	NPC17677
0.703	Intermediate Similarity	NPC193906
0.703	Intermediate Similarity	NPC23080
0.7022	Intermediate Similarity	NPC48624
0.7022	Intermediate Similarity	NPC219917
0.7022	Intermediate Similarity	NPC213659
0.7022	Intermediate Similarity	NPC259166
0.7022	Intermediate Similarity	NPC144118
0.7022	Intermediate Similarity	NPC80962
0.7022	Intermediate Similarity	NPC326109
0.7022	Intermediate Similarity	NPC172250
0.7022	Intermediate Similarity	NPC215311
0.7022	Intermediate Similarity	NPC204985
0.702	Intermediate Similarity	NPC469437
0.7015	Intermediate Similarity	NPC303214
0.701	Intermediate Similarity	NPC309692
0.7009	Intermediate Similarity	NPC119134
0.7006	Intermediate Similarity	NPC279668
0.7006	Intermediate Similarity	NPC12175
0.7006	Intermediate Similarity	NPC309154
0.7006	Intermediate Similarity	NPC278323
0.7006	Intermediate Similarity	NPC55162
0.7006	Intermediate Similarity	NPC90665
0.7	Intermediate Similarity	NPC127996
0.6995	Remote Similarity	NPC77777
0.6994	Remote Similarity	NPC266425
0.6994	Remote Similarity	NPC278556
0.699	Remote Similarity	NPC475147
0.6989	Remote Similarity	NPC161196
0.6985	Remote Similarity	NPC203628
0.6985	Remote Similarity	NPC28510
0.6983	Remote Similarity	NPC26051
0.6983	Remote Similarity	NPC52789
0.6983	Remote Similarity	NPC55832
0.6983	Remote Similarity	NPC469404
0.6983	Remote Similarity	NPC268204
0.6983	Remote Similarity	NPC185607
0.6971	Remote Similarity	NPC286336
0.6971	Remote Similarity	NPC100573
0.6971	Remote Similarity	NPC207873
0.6971	Remote Similarity	NPC125269
0.6966	Remote Similarity	NPC295384
0.6966	Remote Similarity	NPC283429
0.6966	Remote Similarity	NPC136095
0.6965	Remote Similarity	NPC198401
0.6965	Remote Similarity	NPC243626
0.6964	Remote Similarity	NPC476258
0.6964	Remote Similarity	NPC304837
0.6961	Remote Similarity	NPC67904
0.6959	Remote Similarity	NPC70092
0.6959	Remote Similarity	NPC475017
0.6954	Remote Similarity	NPC116007
0.695	Remote Similarity	NPC63152
0.6949	Remote Similarity	NPC228661
0.6949	Remote Similarity	NPC103001
0.6949	Remote Similarity	NPC157855
0.6948	Remote Similarity	NPC169402
0.6946	Remote Similarity	NPC112937
0.6944	Remote Similarity	NPC251071
0.6935	Remote Similarity	NPC301163
0.6935	Remote Similarity	NPC473008
0.6934	Remote Similarity	NPC189661
0.6934	Remote Similarity	NPC116238
0.6932	Remote Similarity	NPC234560
0.6932	Remote Similarity	NPC39426
0.6932	Remote Similarity	NPC99854
0.6927	Remote Similarity	NPC253822
0.6927	Remote Similarity	NPC171094
0.6927	Remote Similarity	NPC101366
0.6927	Remote Similarity	NPC472409
0.6919	Remote Similarity	NPC18306
0.6919	Remote Similarity	NPC10732
0.6914	Remote Similarity	NPC139813
0.6914	Remote Similarity	NPC28753
0.6914	Remote Similarity	NPC82225
0.6914	Remote Similarity	NPC242294
0.6914	Remote Similarity	NPC188646
0.6914	Remote Similarity	NPC337373
0.6914	Remote Similarity	NPC175098
0.6914	Remote Similarity	NPC472365
0.6914	Remote Similarity	NPC294593
0.6914	Remote Similarity	NPC192304
0.6914	Remote Similarity	NPC263670
0.6914	Remote Similarity	NPC312318
0.6914	Remote Similarity	NPC20560
0.6914	Remote Similarity	NPC18877
0.6914	Remote Similarity	NPC56031
0.6914	Remote Similarity	NPC204960
0.6914	Remote Similarity	NPC159623
0.6914	Remote Similarity	NPC144051
0.6911	Remote Similarity	NPC474814
0.6911	Remote Similarity	NPC112336

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 NPC1820 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	696
0.2-0.3	929
0.3-0.4	1507
0.4-0.5	2547
0.5-0.6	2229
0.6-0.7	795
0.7-0.8	91
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.806	Intermediate Similarity	NPD2899	Discontinued
0.799	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD5186	Approved
0.7889	Intermediate Similarity	NPD5183	Approved
0.7871	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD5496	Approved
0.7784	Intermediate Similarity	NPD3297	Approved
0.7677	Intermediate Similarity	NPD3298	Approved
0.7656	Intermediate Similarity	NPD5937	Approved
0.7576	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6874	Approved
0.7487	Intermediate Similarity	NPD3793	Phase 3
0.7377	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2654	Approved
0.733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2246	Approved
0.7326	Intermediate Similarity	NPD2248	Approved
0.7321	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4539	Phase 1
0.7233	Intermediate Similarity	NPD5860	Discontinued
0.7231	Intermediate Similarity	NPD5620	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2796	Approved
0.7178	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7654	Discontinued
0.7156	Intermediate Similarity	NPD6198	Phase 1
0.715	Intermediate Similarity	NPD4979	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD683	Approved
0.7098	Intermediate Similarity	NPD6104	Discontinued
0.7092	Intermediate Similarity	NPD4515	Suspended
0.7083	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4981	Phase 2
0.7059	Intermediate Similarity	NPD7626	Approved
0.7059	Intermediate Similarity	NPD7627	Approved
0.7045	Intermediate Similarity	NPD6625	Approved
0.7031	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5071	Phase 2
0.7027	Intermediate Similarity	NPD4846	Phase 2
0.702	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6790	Phase 1
0.7	Intermediate Similarity	NPD5242	Approved
0.699	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8461	Discontinued
0.698	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4082	Approved
0.6964	Remote Similarity	NPD4613	Phase 2
0.6959	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4668	Phase 2
0.6932	Remote Similarity	NPD1510	Phase 2
0.6931	Remote Similarity	NPD4361	Phase 2
0.6931	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7225	Discontinued
0.6915	Remote Similarity	NPD955	Approved
0.6907	Remote Similarity	NPD7479	Phase 2
0.6905	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1240	Approved
0.6897	Remote Similarity	NPD5515	Phase 2
0.6895	Remote Similarity	NPD6457	Approved
0.6895	Remote Similarity	NPD2249	Approved
0.6895	Remote Similarity	NPD2821	Approved
0.6895	Remote Similarity	NPD2247	Approved
0.6893	Remote Similarity	NPD5006	Approved
0.6893	Remote Similarity	NPD5005	Approved
0.6893	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3252	Approved
0.6872	Remote Similarity	NPD1945	Phase 1
0.6856	Remote Similarity	NPD3965	Phase 1
0.6856	Remote Similarity	NPD6020	Phase 2
0.6848	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6321	Discontinued
0.6842	Remote Similarity	NPD7584	Approved
0.6831	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1483	Discontinued
0.6828	Remote Similarity	NPD2366	Approved
0.6827	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD4465	Phase 2
0.6827	Remote Similarity	NPD4467	Phase 2
0.6822	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1607	Approved
0.6818	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3259	Approved
0.6811	Remote Similarity	NPD6357	Discontinued
0.6809	Remote Similarity	NPD5978	Approved
0.6809	Remote Similarity	NPD5977	Approved
0.6804	Remote Similarity	NPD7545	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1898	Discontinued
0.68	Remote Similarity	NPD3140	Approved
0.68	Remote Similarity	NPD3142	Approved
0.6798	Remote Similarity	NPD4363	Phase 3
0.6798	Remote Similarity	NPD4360	Phase 2
0.6792	Remote Similarity	NPD4493	Discontinued
0.6786	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7417	Discontinued
0.6776	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7559	Phase 2
0.6774	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7263	Phase 2
0.6762	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4596	Phase 1
0.6757	Remote Similarity	NPD4952	Phase 3
0.6751	Remote Similarity	NPD3386	Phase 2
0.6745	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5889	Approved
0.6738	Remote Similarity	NPD5890	Approved
0.6737	Remote Similarity	NPD1307	Phase 2
0.6737	Remote Similarity	NPD1309	Phase 2
0.673	Remote Similarity	NPD2907	Approved
0.673	Remote Similarity	NPD2906	Approved
0.673	Remote Similarity	NPD3472	Approved
0.673	Remote Similarity	NPD4022	Approved
0.673	Remote Similarity	NPD4859	Phase 1
0.6726	Remote Similarity	NPD6962	Phase 2
0.6714	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4420	Approved
0.6699	Remote Similarity	NPD5194	Approved
0.6699	Remote Similarity	NPD5513	Phase 2
0.6699	Remote Similarity	NPD5196	Approved
0.6699	Remote Similarity	NPD5197	Approved
0.6699	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7186	Phase 3
0.6697	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD743	Approved
0.6684	Remote Similarity	NPD6585	Discontinued
0.6683	Remote Similarity	NPD5928	Phase 1
0.6667	Remote Similarity	NPD4373	Phase 2
0.6667	Remote Similarity	NPD3372	Discontinued
0.6667	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3446	Phase 1
0.6667	Remote Similarity	NPD7803	Approved
0.6667	Remote Similarity	NPD5823	Approved
0.6667	Remote Similarity	NPD5637	Discontinued
0.6667	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD2300	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6386	Approved
0.6649	Remote Similarity	NPD6385	Approved
0.6649	Remote Similarity	NPD1913	Phase 1
0.6635	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2339	Phase 3
0.6633	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD3229	Phase 2
0.663	Remote Similarity	NPD1549	Phase 2
0.6621	Remote Similarity	NPD3437	Discontinued
0.6619	Remote Similarity	NPD3802	Phase 3
0.6619	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6844	Discontinued
0.6607	Remote Similarity	NPD6199	Discontinued
0.6605	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4494	Approved
0.6605	Remote Similarity	NPD4492	Approved
0.6604	Remote Similarity	NPD6296	Discontinued
0.6602	Remote Similarity	NPD3964	Approved
0.66	Remote Similarity	NPD7546	Discontinued
0.6599	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6788	Approved
0.6596	Remote Similarity	NPD4380	Phase 2
0.6595	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7922	Phase 1
0.6592	Remote Similarity	NPD2670	Approved
0.6589	Remote Similarity	NPD5914	Approved
0.6589	Remote Similarity	NPD3893	Discontinued
0.6588	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD8067	Phase 3
0.6575	Remote Similarity	NPD7752	Approved
0.6575	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7753	Approved
0.6575	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4642	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5195	Discontinued
0.6569	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4586	Phase 3
0.6564	Remote Similarity	NPD2216	Approved
0.6564	Remote Similarity	NPD2215	Approved
0.6562	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6719	Approved
0.6552	Remote Similarity	NPD2792	Approved
0.655	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD2681	Approved
0.6546	Remote Similarity	NPD2680	Approved
0.6545	Remote Similarity	NPD6242	Discontinued
0.6544	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6799	Approved
0.6535	Remote Similarity	NPD3153	Approved
0.6535	Remote Similarity	NPD3154	Approved
0.6533	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3912	Discontinued
0.653	Remote Similarity	NPD5632	Approved
0.6528	Remote Similarity	NPD3888	Discontinued
0.6526	Remote Similarity	NPD6279	Approved
0.6526	Remote Similarity	NPD7043	Discontinued
0.6526	Remote Similarity	NPD7583	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