NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.14
Volume:	259.928
LogP:	1.111
LogD:	1.15
LogS:	-2.665
# Rotatable Bonds:	1
TPSA:	58.88
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	5.21
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.575
MDCK Permeability:	5.243458417680813e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	73.90784454345703%
Volume Distribution (VD):	1.123
Pgp-substrate:	20.794384002685547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.261
CYP1A2-substrate:	0.667
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.176
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.256
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.393
CYP3A4-inhibitor:	0.769
CYP3A4-substrate:	0.376

ADMET: Excretion

Clearance (CL):	3.904
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.321
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.206
Rat Oral Acute Toxicity:	0.728
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.087
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC32028

Natural Product ID:	NPC32028
*Common Name:**	IZGRHSRWTILCID-FIXISWKDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IZGRHSRWTILCID-FIXISWKDSA-N
Standard InCHI:	InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10-11H,1,7-8,16H2,2H3,(H,17,18)/t10-,11+,15+/m0/s1
SMILES:	CC1=C[C@@H]2[C@H]([C@@](C1)(N)c1ccc(nc1C2)O)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409142
PubChem CID:	10198698
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives

*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
NPO32769	lycopodiastrum casuarinoides	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23941108]

☑ 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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	489.0	nM	PMID[486676]

☑ 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 NPC32028 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	464
0.1-0.2	3061
0.2-0.3	12781
0.3-0.4	12155
0.4-0.5	9246
0.5-0.6	3575
0.6-0.7	1291
0.7-0.8	105
0.8-0.85	1
0.85-0.9	6
0.9-0.95	4
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC315214
0.9933	High Similarity	NPC47298
0.9867	High Similarity	NPC159319
0.9613	High Similarity	NPC259545
0.961	High Similarity	NPC126481
0.9371	High Similarity	NPC232340
0.9241	High Similarity	NPC471294
0.8848	High Similarity	NPC133306
0.8713	High Similarity	NPC45850
0.8588	High Similarity	NPC183805
0.8312	Intermediate Similarity	NPC60553
0.7988	Intermediate Similarity	NPC84508
0.7987	Intermediate Similarity	NPC161292
0.7844	Intermediate Similarity	NPC473057
0.7803	Intermediate Similarity	NPC88363
0.7791	Intermediate Similarity	NPC153769
0.7785	Intermediate Similarity	NPC245657
0.7753	Intermediate Similarity	NPC246700
0.7753	Intermediate Similarity	NPC128751
0.7722	Intermediate Similarity	NPC280853
0.7709	Intermediate Similarity	NPC469497
0.7709	Intermediate Similarity	NPC106833
0.7701	Intermediate Similarity	NPC72980
0.7697	Intermediate Similarity	NPC206186
0.7684	Intermediate Similarity	NPC94943
0.7673	Intermediate Similarity	NPC285016
0.767	Intermediate Similarity	NPC212535
0.7658	Intermediate Similarity	NPC471596
0.7627	Intermediate Similarity	NPC190007
0.7572	Intermediate Similarity	NPC474409
0.7557	Intermediate Similarity	NPC478032
0.7547	Intermediate Similarity	NPC471594
0.7531	Intermediate Similarity	NPC471598
0.7529	Intermediate Similarity	NPC97367
0.75	Intermediate Similarity	NPC44161
0.7486	Intermediate Similarity	NPC288943
0.7485	Intermediate Similarity	NPC471178
0.7471	Intermediate Similarity	NPC124542
0.7471	Intermediate Similarity	NPC471177
0.7471	Intermediate Similarity	NPC59779
0.7468	Intermediate Similarity	NPC278451
0.7459	Intermediate Similarity	NPC153042
0.7455	Intermediate Similarity	NPC288445
0.7443	Intermediate Similarity	NPC283152
0.744	Intermediate Similarity	NPC141353
0.7433	Intermediate Similarity	NPC249040
0.7429	Intermediate Similarity	NPC303225
0.7425	Intermediate Similarity	NPC26872
0.7414	Intermediate Similarity	NPC105758
0.7414	Intermediate Similarity	NPC476686
0.7414	Intermediate Similarity	NPC476688
0.7389	Intermediate Similarity	NPC476319
0.7374	Intermediate Similarity	NPC19679
0.7366	Intermediate Similarity	NPC474188
0.7348	Intermediate Similarity	NPC171171
0.7344	Intermediate Similarity	NPC477111
0.7337	Intermediate Similarity	NPC141915
0.7337	Intermediate Similarity	NPC114335
0.7337	Intermediate Similarity	NPC280964
0.7333	Intermediate Similarity	NPC320394
0.7333	Intermediate Similarity	NPC204717
0.7308	Intermediate Similarity	NPC66083
0.7299	Intermediate Similarity	NPC278874
0.7294	Intermediate Similarity	NPC26850
0.7293	Intermediate Similarity	NPC314002
0.7278	Intermediate Similarity	NPC220765
0.7277	Intermediate Similarity	NPC475070
0.7273	Intermediate Similarity	NPC70956
0.7273	Intermediate Similarity	NPC243834
0.7273	Intermediate Similarity	NPC208060
0.7256	Intermediate Similarity	NPC470403
0.7256	Intermediate Similarity	NPC470404
0.7256	Intermediate Similarity	NPC470394
0.7254	Intermediate Similarity	NPC470931
0.7254	Intermediate Similarity	NPC475910
0.7253	Intermediate Similarity	NPC194040
0.7253	Intermediate Similarity	NPC314573
0.7249	Intermediate Similarity	NPC329747
0.7249	Intermediate Similarity	NPC329793
0.7241	Intermediate Similarity	NPC98187
0.7241	Intermediate Similarity	NPC108469
0.724	Intermediate Similarity	NPC477113
0.7238	Intermediate Similarity	NPC62069
0.7228	Intermediate Similarity	NPC3715
0.7225	Intermediate Similarity	NPC223427
0.7216	Intermediate Similarity	NPC158129
0.7213	Intermediate Similarity	NPC46580
0.7204	Intermediate Similarity	NPC329541
0.72	Intermediate Similarity	NPC154293
0.7198	Intermediate Similarity	NPC42591
0.7173	Intermediate Similarity	NPC475112
0.7173	Intermediate Similarity	NPC475085
0.7173	Intermediate Similarity	NPC291535
0.7172	Intermediate Similarity	NPC330009
0.7172	Intermediate Similarity	NPC469928
0.7169	Intermediate Similarity	NPC470395
0.7168	Intermediate Similarity	NPC224632
0.7168	Intermediate Similarity	NPC177404
0.7159	Intermediate Similarity	NPC473764
0.7159	Intermediate Similarity	NPC314940
0.7157	Intermediate Similarity	NPC478074
0.7151	Intermediate Similarity	NPC324149
0.7151	Intermediate Similarity	NPC99666
0.7135	Intermediate Similarity	NPC189812
0.7135	Intermediate Similarity	NPC329688
0.7135	Intermediate Similarity	NPC95783
0.7128	Intermediate Similarity	NPC476116
0.7127	Intermediate Similarity	NPC144114
0.712	Intermediate Similarity	NPC254762
0.7113	Intermediate Similarity	NPC193777
0.7111	Intermediate Similarity	NPC67659
0.7105	Intermediate Similarity	NPC476167
0.7102	Intermediate Similarity	NPC317430
0.7088	Intermediate Similarity	NPC176127
0.7085	Intermediate Similarity	NPC183407
0.7083	Intermediate Similarity	NPC257142
0.7081	Intermediate Similarity	NPC32771
0.7079	Intermediate Similarity	NPC34508
0.7074	Intermediate Similarity	NPC276517
0.7069	Intermediate Similarity	NPC16667
0.7065	Intermediate Similarity	NPC61350
0.7062	Intermediate Similarity	NPC280548
0.7056	Intermediate Similarity	NPC184964
0.7053	Intermediate Similarity	NPC306376
0.7053	Intermediate Similarity	NPC192315
0.7049	Intermediate Similarity	NPC84478
0.7047	Intermediate Similarity	NPC476098
0.7039	Intermediate Similarity	NPC312872
0.7037	Intermediate Similarity	NPC205403
0.7035	Intermediate Similarity	NPC285469
0.7033	Intermediate Similarity	NPC314394
0.7033	Intermediate Similarity	NPC477891
0.7031	Intermediate Similarity	NPC267423
0.7029	Intermediate Similarity	NPC118511
0.702	Intermediate Similarity	NPC294620
0.702	Intermediate Similarity	NPC48353
0.7018	Intermediate Similarity	NPC36168
0.7016	Intermediate Similarity	NPC128823
0.7011	Intermediate Similarity	NPC131718
0.7005	Intermediate Similarity	NPC469390
0.7	Intermediate Similarity	NPC150048
0.7	Intermediate Similarity	NPC77555
0.7	Intermediate Similarity	NPC134586
0.7	Intermediate Similarity	NPC203754
0.7	Intermediate Similarity	NPC477110
0.699	Remote Similarity	NPC18348
0.6989	Remote Similarity	NPC242928
0.6984	Remote Similarity	NPC195314
0.6983	Remote Similarity	NPC313791
0.6983	Remote Similarity	NPC472123
0.6979	Remote Similarity	NPC11017
0.6974	Remote Similarity	NPC474145
0.6974	Remote Similarity	NPC475841
0.697	Remote Similarity	NPC220337
0.697	Remote Similarity	NPC9894
0.697	Remote Similarity	NPC208284
0.6966	Remote Similarity	NPC164664
0.6961	Remote Similarity	NPC96890
0.6961	Remote Similarity	NPC211997
0.6961	Remote Similarity	NPC162748
0.6959	Remote Similarity	NPC284348
0.6947	Remote Similarity	NPC242209
0.6947	Remote Similarity	NPC70259
0.6947	Remote Similarity	NPC472193
0.6941	Remote Similarity	NPC124005
0.6936	Remote Similarity	NPC184476
0.6932	Remote Similarity	NPC476118
0.6931	Remote Similarity	NPC289786
0.6927	Remote Similarity	NPC32200
0.6927	Remote Similarity	NPC280714
0.6927	Remote Similarity	NPC476175
0.6923	Remote Similarity	NPC164374
0.6923	Remote Similarity	NPC270009
0.6923	Remote Similarity	NPC137929
0.6919	Remote Similarity	NPC5145
0.6919	Remote Similarity	NPC471304
0.6911	Remote Similarity	NPC156704
0.6908	Remote Similarity	NPC6215
0.6905	Remote Similarity	NPC242556
0.6897	Remote Similarity	NPC116573
0.6895	Remote Similarity	NPC43787
0.6895	Remote Similarity	NPC205934
0.6888	Remote Similarity	NPC304183
0.6888	Remote Similarity	NPC476106
0.6885	Remote Similarity	NPC198339
0.6881	Remote Similarity	NPC304926
0.6881	Remote Similarity	NPC476041
0.6879	Remote Similarity	NPC38736
0.6879	Remote Similarity	NPC207726
0.6875	Remote Similarity	NPC72211
0.6872	Remote Similarity	NPC477135
0.6868	Remote Similarity	NPC151939
0.6857	Remote Similarity	NPC67056
0.6856	Remote Similarity	NPC476044
0.6853	Remote Similarity	NPC53344
0.6853	Remote Similarity	NPC270918
0.6848	Remote Similarity	NPC192270
0.6842	Remote Similarity	NPC307963
0.6842	Remote Similarity	NPC37548
0.6837	Remote Similarity	NPC470500

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 NPC32028 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	643
0.2-0.3	857
0.3-0.4	1207
0.4-0.5	3081
0.5-0.6	2461
0.6-0.7	564
0.7-0.8	51
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9933	High Similarity	NPD1685	Approved
0.9933	High Similarity	NPD1684	Approved
0.8315	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD925	Approved
0.7692	Intermediate Similarity	NPD926	Approved
0.7683	Intermediate Similarity	NPD6158	Phase 2
0.7683	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1325	Approved
0.7661	Intermediate Similarity	NPD1326	Approved
0.7609	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2882	Phase 1
0.7568	Intermediate Similarity	NPD2176	Approved
0.7568	Intermediate Similarity	NPD2175	Phase 3
0.7568	Intermediate Similarity	NPD2177	Approved
0.7543	Intermediate Similarity	NPD6159	Phase 2
0.75	Intermediate Similarity	NPD2383	Phase 1
0.7469	Intermediate Similarity	NPD3525	Discontinued
0.7442	Intermediate Similarity	NPD425	Approved
0.7442	Intermediate Similarity	NPD424	Approved
0.7435	Intermediate Similarity	NPD2916	Discontinued
0.7416	Intermediate Similarity	NPD4204	Approved
0.7416	Intermediate Similarity	NPD4203	Approved
0.7414	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD5939	Approved
0.7409	Intermediate Similarity	NPD5936	Approved
0.7401	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4511	Phase 1
0.7351	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD863	Approved
0.7326	Intermediate Similarity	NPD861	Approved
0.7326	Intermediate Similarity	NPD862	Approved
0.7301	Intermediate Similarity	NPD1592	Phase 3
0.7293	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2381	Approved
0.7288	Intermediate Similarity	NPD2380	Approved
0.7288	Intermediate Similarity	NPD5100	Phase 3
0.7288	Intermediate Similarity	NPD2382	Approved
0.7287	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7474	Suspended
0.7251	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5255	Approved
0.7232	Intermediate Similarity	NPD6492	Phase 2
0.7232	Intermediate Similarity	NPD5065	Approved
0.7225	Intermediate Similarity	NPD4044	Discontinued
0.7207	Intermediate Similarity	NPD3920	Phase 2
0.7204	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6290	Phase 2
0.72	Intermediate Similarity	NPD2781	Approved
0.7193	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4703	Approved
0.7186	Intermediate Similarity	NPD4702	Approved
0.7184	Intermediate Similarity	NPD2782	Approved
0.7184	Intermediate Similarity	NPD2780	Approved
0.7175	Intermediate Similarity	NPD7418	Discontinued
0.7165	Intermediate Similarity	NPD6376	Discontinued
0.7143	Intermediate Similarity	NPD4502	Phase 2
0.7143	Intermediate Similarity	NPD2727	Phase 2
0.7143	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD444	Approved
0.7113	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3417	Phase 1
0.7108	Intermediate Similarity	NPD3813	Approved
0.7105	Intermediate Similarity	NPD8395	Approved
0.7105	Intermediate Similarity	NPD8396	Approved
0.7104	Intermediate Similarity	NPD2762	Phase 2
0.7095	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7948	Phase 1
0.7086	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3404	Approved
0.7045	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3814	Phase 1
0.7006	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3928	Approved
0.6995	Remote Similarity	NPD3931	Approved
0.6984	Remote Similarity	NPD6590	Discontinued
0.6977	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5530	Phase 1
0.6961	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6281	Approved
0.6946	Remote Similarity	NPD3717	Discontinued
0.6944	Remote Similarity	NPD9690	Approved
0.6937	Remote Similarity	NPD947	Approved
0.6935	Remote Similarity	NPD3330	Phase 1
0.6932	Remote Similarity	NPD5140	Approved
0.6932	Remote Similarity	NPD5138	Approved
0.6931	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD9705	Discontinued
0.6914	Remote Similarity	NPD112	Approved
0.691	Remote Similarity	NPD2844	Phase 3
0.6907	Remote Similarity	NPD6975	Discontinued
0.6904	Remote Similarity	NPD7671	Approved
0.6904	Remote Similarity	NPD7672	Approved
0.6889	Remote Similarity	NPD3224	Phase 2
0.6875	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6991	Approved
0.6853	Remote Similarity	NPD7222	Phase 2
0.6852	Remote Similarity	NPD1251	Discontinued
0.6848	Remote Similarity	NPD7867	Phase 1
0.6842	Remote Similarity	NPD1038	Approved
0.6839	Remote Similarity	NPD6026	Approved
0.6831	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7726	Phase 1
0.6828	Remote Similarity	NPD4889	Approved
0.6828	Remote Similarity	NPD6227	Discontinued
0.6828	Remote Similarity	NPD3082	Discontinued
0.6825	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5913	Phase 3
0.6818	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3243	Approved
0.6811	Remote Similarity	NPD5596	Phase 2
0.6807	Remote Similarity	NPD852	Discontinued
0.6806	Remote Similarity	NPD6251	Discontinued
0.6802	Remote Similarity	NPD4463	Approved
0.6802	Remote Similarity	NPD4462	Approved
0.68	Remote Similarity	NPD2581	Approved
0.68	Remote Similarity	NPD2582	Approved
0.68	Remote Similarity	NPD6220	Phase 3
0.6796	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5256	Discontinued
0.6789	Remote Similarity	NPD3921	Approved
0.6789	Remote Similarity	NPD6569	Phase 2
0.6789	Remote Similarity	NPD3923	Approved
0.6789	Remote Similarity	NPD3922	Approved
0.6789	Remote Similarity	NPD3924	Approved
0.6788	Remote Similarity	NPD1254	Approved
0.6788	Remote Similarity	NPD1253	Approved
0.6788	Remote Similarity	NPD1255	Approved
0.6788	Remote Similarity	NPD1256	Approved
0.6786	Remote Similarity	NPD4886	Phase 2
0.6786	Remote Similarity	NPD5020	Approved
0.6771	Remote Similarity	NPD5512	Phase 3
0.6771	Remote Similarity	NPD6594	Discontinued
0.6768	Remote Similarity	NPD5429	Discontinued
0.6766	Remote Similarity	NPD2794	Discontinued
0.6765	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD9695	Approved
0.6754	Remote Similarity	NPD6361	Phase 2
0.6754	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD802	Phase 2
0.6751	Remote Similarity	NPD4039	Approved
0.6751	Remote Similarity	NPD4034	Approved
0.6751	Remote Similarity	NPD4037	Approved
0.6751	Remote Similarity	NPD31	Approved
0.6751	Remote Similarity	NPD4122	Approved
0.6751	Remote Similarity	NPD4795	Phase 2
0.6751	Remote Similarity	NPD4038	Approved
0.6751	Remote Similarity	NPD4033	Approved
0.6751	Remote Similarity	NPD32	Approved
0.6751	Remote Similarity	NPD4035	Approved
0.6751	Remote Similarity	NPD4036	Approved
0.6749	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD2616	Phase 3
0.6733	Remote Similarity	NPD2615	Phase 3
0.6725	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.672	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1739	Approved
0.6718	Remote Similarity	NPD484	Approved
0.6718	Remote Similarity	NPD1740	Approved
0.6718	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD9284	Approved
0.6708	Remote Similarity	NPD9080	Approved
0.6708	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4375	Approved
0.6701	Remote Similarity	NPD7419	Discontinued
0.6685	Remote Similarity	NPD4071	Approved
0.6685	Remote Similarity	NPD4072	Approved
0.6684	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7452	Approved
0.6683	Remote Similarity	NPD7453	Approved
0.6667	Remote Similarity	NPD7112	Discontinued
0.6667	Remote Similarity	NPD4551	Phase 2
0.6667	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5428	Discontinued
0.665	Remote Similarity	NPD6208	Discontinued
0.665	Remote Similarity	NPD5658	Approved
0.6649	Remote Similarity	NPD5003	Discontinued
0.6649	Remote Similarity	NPD2952	Discontinued
0.6649	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5680	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