NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	255.1
Volume:	238.416
LogP:	-1.34
LogD:	-0.936
LogS:	-0.871
# Rotatable Bonds:	3
TPSA:	116.89
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	3.869
Fsp3:	0.455
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:	-5.721
MDCK Permeability:	0.0003854148380924016
Pgp-inhibitor:	0.0
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.904
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	10.467460632324219%
Volume Distribution (VD):	0.433
Pgp-substrate:	93.00625610351562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.001
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	4.862
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.06
Carcinogencity:	0.192
Eye Corrosion:	0.003
Eye Irritation:	0.113
Respiratory Toxicity:	0.007

Download Data

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

Natural Product: NPC138018

Natural Product ID:	NPC138018
*Common Name:**	Nicotinamide Riboside
IUPAC Name:	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridin-1-ium-3-carboxamide
Synonyms:	Nicotinamide riboside
Standard InCHIKey:	JLEBZPBDRKPWTD-TURQNECASA-O
Standard InCHI:	InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1-4,7-9,11,14-16H,5H2,(H-,12,17)/p+1/t7-,8-,9-,11-/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)[n+]1cccc(c1)C(=N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL438497
PubChem CID:	439924
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002203] Glycosylamines

*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

☑ 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	2
Others	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
ORGANISM	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	1.7	%	PMID[487758]
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	111.0	%	PMID[487758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.7	%	PMID[487758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.6	%	PMID[487758]
NPT27	Others	Unspecified		Activity	=	123.0	%	PMID[487758]
NPT27	Others	Unspecified		Activity	=	107.0	%	PMID[487758]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[487759]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[487759]

☑ 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 NPC138018 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	321
0.1-0.2	3141
0.2-0.3	13544
0.3-0.4	16782
0.4-0.5	5083
0.5-0.6	2833
0.6-0.7	944
0.7-0.8	44
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9539	High Similarity	NPC319456
0.8712	High Similarity	NPC317010
0.8276	Intermediate Similarity	NPC165370
0.8276	Intermediate Similarity	NPC306397
0.8199	Intermediate Similarity	NPC71079
0.8151	Intermediate Similarity	NPC212125
0.8148	Intermediate Similarity	NPC474217
0.8098	Intermediate Similarity	NPC85918
0.8079	Intermediate Similarity	NPC29702
0.8049	Intermediate Similarity	NPC278366
0.8049	Intermediate Similarity	NPC127730
0.7861	Intermediate Similarity	NPC62510
0.7722	Intermediate Similarity	NPC471323
0.7669	Intermediate Similarity	NPC263455
0.7541	Intermediate Similarity	NPC474767
0.7485	Intermediate Similarity	NPC322976
0.7485	Intermediate Similarity	NPC324203
0.7485	Intermediate Similarity	NPC63338
0.743	Intermediate Similarity	NPC75544
0.7418	Intermediate Similarity	NPC20593
0.7394	Intermediate Similarity	NPC312860
0.7365	Intermediate Similarity	NPC269919
0.7365	Intermediate Similarity	NPC132680
0.7349	Intermediate Similarity	NPC63562
0.7345	Intermediate Similarity	NPC325093
0.7312	Intermediate Similarity	NPC318935
0.7297	Intermediate Similarity	NPC59033
0.7294	Intermediate Similarity	NPC263439
0.729	Intermediate Similarity	NPC315320
0.7278	Intermediate Similarity	NPC328029
0.7263	Intermediate Similarity	NPC318020
0.7247	Intermediate Similarity	NPC322043
0.7247	Intermediate Similarity	NPC327373
0.7239	Intermediate Similarity	NPC167400
0.7225	Intermediate Similarity	NPC256828
0.7214	Intermediate Similarity	NPC107160
0.7204	Intermediate Similarity	NPC317672
0.7204	Intermediate Similarity	NPC149708
0.7195	Intermediate Similarity	NPC220523
0.7193	Intermediate Similarity	NPC102423
0.719	Intermediate Similarity	NPC151489
0.7186	Intermediate Similarity	NPC107287
0.7184	Intermediate Similarity	NPC470498
0.7182	Intermediate Similarity	NPC328798
0.7159	Intermediate Similarity	NPC150048
0.7159	Intermediate Similarity	NPC203754
0.7151	Intermediate Similarity	NPC329024
0.7151	Intermediate Similarity	NPC471178
0.7143	Intermediate Similarity	NPC182814
0.7134	Intermediate Similarity	NPC324611
0.7134	Intermediate Similarity	NPC256893
0.7134	Intermediate Similarity	NPC174421
0.7128	Intermediate Similarity	NPC79223
0.7126	Intermediate Similarity	NPC153769
0.7126	Intermediate Similarity	NPC222174
0.7125	Intermediate Similarity	NPC114310
0.711	Intermediate Similarity	NPC125659
0.711	Intermediate Similarity	NPC168702
0.7097	Intermediate Similarity	NPC292361
0.7097	Intermediate Similarity	NPC471311
0.7097	Intermediate Similarity	NPC471313
0.7093	Intermediate Similarity	NPC78375
0.7093	Intermediate Similarity	NPC469813
0.7093	Intermediate Similarity	NPC211187
0.7093	Intermediate Similarity	NPC476446
0.7088	Intermediate Similarity	NPC325775
0.7076	Intermediate Similarity	NPC131718
0.7073	Intermediate Similarity	NPC230085
0.7073	Intermediate Similarity	NPC159630
0.7068	Intermediate Similarity	NPC25442
0.7068	Intermediate Similarity	NPC12944
0.7065	Intermediate Similarity	NPC127647
0.7059	Intermediate Similarity	NPC212742
0.7056	Intermediate Similarity	NPC48938
0.7021	Intermediate Similarity	NPC320748
0.7021	Intermediate Similarity	NPC324245
0.7017	Intermediate Similarity	NPC207851
0.7011	Intermediate Similarity	NPC98187
0.7011	Intermediate Similarity	NPC108469
0.7	Intermediate Similarity	NPC32451
0.7	Intermediate Similarity	NPC328559
0.6995	Remote Similarity	NPC156044
0.6994	Remote Similarity	NPC473057
0.6989	Remote Similarity	NPC158129
0.6988	Remote Similarity	NPC161292
0.6981	Remote Similarity	NPC322488
0.6978	Remote Similarity	NPC188387
0.6978	Remote Similarity	NPC163421
0.6966	Remote Similarity	NPC476419
0.6961	Remote Similarity	NPC244536
0.6961	Remote Similarity	NPC469358
0.6949	Remote Similarity	NPC313791
0.6946	Remote Similarity	NPC112741
0.6943	Remote Similarity	NPC309498
0.6936	Remote Similarity	NPC471177
0.6936	Remote Similarity	NPC124542
0.6936	Remote Similarity	NPC59779
0.6923	Remote Similarity	NPC472752
0.6919	Remote Similarity	NPC113812
0.6919	Remote Similarity	NPC230869
0.6906	Remote Similarity	NPC314394
0.6897	Remote Similarity	NPC162268
0.6897	Remote Similarity	NPC97367
0.6895	Remote Similarity	NPC160127
0.6895	Remote Similarity	NPC50997
0.6893	Remote Similarity	NPC273532
0.6889	Remote Similarity	NPC141377
0.685	Remote Similarity	NPC472285
0.6833	Remote Similarity	NPC211997
0.6831	Remote Similarity	NPC284559
0.6818	Remote Similarity	NPC54988
0.6818	Remote Similarity	NPC292517
0.6818	Remote Similarity	NPC265605
0.6818	Remote Similarity	NPC48564
0.6818	Remote Similarity	NPC111732
0.6818	Remote Similarity	NPC182570
0.68	Remote Similarity	NPC40779
0.68	Remote Similarity	NPC311276
0.68	Remote Similarity	NPC288349
0.6795	Remote Similarity	NPC27740
0.6786	Remote Similarity	NPC63041
0.6781	Remote Similarity	NPC76540
0.6778	Remote Similarity	NPC134586
0.6776	Remote Similarity	NPC297486
0.6776	Remote Similarity	NPC240136
0.6776	Remote Similarity	NPC471402
0.6757	Remote Similarity	NPC27802
0.6735	Remote Similarity	NPC316403
0.6734	Remote Similarity	NPC476467
0.673	Remote Similarity	NPC89490
0.6723	Remote Similarity	NPC41717
0.6721	Remote Similarity	NPC219963
0.6721	Remote Similarity	NPC71037
0.6721	Remote Similarity	NPC161887
0.672	Remote Similarity	NPC79293
0.672	Remote Similarity	NPC279401
0.672	Remote Similarity	NPC289786
0.672	Remote Similarity	NPC46580
0.6718	Remote Similarity	NPC470500
0.6717	Remote Similarity	NPC5145
0.6716	Remote Similarity	NPC30570
0.6708	Remote Similarity	NPC471322
0.6707	Remote Similarity	NPC471312
0.6703	Remote Similarity	NPC295158
0.6703	Remote Similarity	NPC314002
0.6703	Remote Similarity	NPC133261
0.6702	Remote Similarity	NPC114974
0.6687	Remote Similarity	NPC475105
0.6687	Remote Similarity	NPC475090
0.6687	Remote Similarity	NPC329896
0.6685	Remote Similarity	NPC220765
0.6685	Remote Similarity	NPC472110
0.6685	Remote Similarity	NPC472122
0.6685	Remote Similarity	NPC472444
0.6685	Remote Similarity	NPC472109
0.6685	Remote Similarity	NPC24594
0.6684	Remote Similarity	NPC209917
0.6683	Remote Similarity	NPC162812
0.6683	Remote Similarity	NPC475408
0.6683	Remote Similarity	NPC471014
0.6667	Remote Similarity	NPC52831
0.6667	Remote Similarity	NPC472284
0.6667	Remote Similarity	NPC212213
0.6667	Remote Similarity	NPC469762
0.6667	Remote Similarity	NPC41333
0.6667	Remote Similarity	NPC472550
0.6667	Remote Similarity	NPC129721
0.6667	Remote Similarity	NPC48042
0.6667	Remote Similarity	NPC315555
0.6667	Remote Similarity	NPC325705
0.6667	Remote Similarity	NPC171171
0.6667	Remote Similarity	NPC304179
0.6667	Remote Similarity	NPC477975
0.665	Remote Similarity	NPC144779
0.665	Remote Similarity	NPC472553
0.665	Remote Similarity	NPC294579
0.6649	Remote Similarity	NPC204717
0.6649	Remote Similarity	NPC284678
0.6649	Remote Similarity	NPC95783
0.6648	Remote Similarity	NPC326575
0.6648	Remote Similarity	NPC96890
0.6648	Remote Similarity	NPC184964
0.6635	Remote Similarity	NPC476492
0.6634	Remote Similarity	NPC470306
0.6634	Remote Similarity	NPC477910
0.6632	Remote Similarity	NPC226202
0.6629	Remote Similarity	NPC84508
0.6627	Remote Similarity	NPC159856
0.6624	Remote Similarity	NPC290094
0.6618	Remote Similarity	NPC250178
0.6617	Remote Similarity	NPC229348
0.6612	Remote Similarity	NPC472443
0.6609	Remote Similarity	NPC469785
0.6601	Remote Similarity	NPC6981
0.6601	Remote Similarity	NPC471016
0.6599	Remote Similarity	NPC472286
0.6599	Remote Similarity	NPC472287
0.6598	Remote Similarity	NPC470497
0.6596	Remote Similarity	NPC472289
0.6591	Remote Similarity	NPC25899

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 NPC138018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	605
0.2-0.3	882
0.3-0.4	1664
0.4-0.5	3250
0.5-0.6	2075
0.6-0.7	485
0.7-0.8	30
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8412	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD9506	Approved
0.8276	Intermediate Similarity	NPD9080	Approved
0.8151	Intermediate Similarity	NPD9284	Approved
0.7974	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1649	Discontinued
0.7722	Intermediate Similarity	NPD1352	Discontinued
0.7658	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1380	Discovery
0.75	Intermediate Similarity	NPD3813	Approved
0.7485	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1383	Phase 3
0.7484	Intermediate Similarity	NPD1382	Phase 2
0.7425	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD9382	Approved
0.7365	Intermediate Similarity	NPD9383	Approved
0.729	Intermediate Similarity	NPD9207	Approved
0.729	Intermediate Similarity	NPD9206	Approved
0.7262	Intermediate Similarity	NPD820	Phase 3
0.7239	Intermediate Similarity	NPD9075	Approved
0.7239	Intermediate Similarity	NPD9074	Approved
0.7229	Intermediate Similarity	NPD510	Phase 1
0.7219	Intermediate Similarity	NPD5255	Approved
0.7207	Intermediate Similarity	NPD1096	Discontinued
0.7191	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3082	Discontinued
0.716	Intermediate Similarity	NPD2582	Approved
0.716	Intermediate Similarity	NPD2581	Approved
0.7158	Intermediate Similarity	NPD4699	Discontinued
0.7143	Intermediate Similarity	NPD4021	Phase 2
0.7081	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7396	Approved
0.7056	Intermediate Similarity	NPD5596	Phase 2
0.7048	Intermediate Similarity	NPD4702	Approved
0.7048	Intermediate Similarity	NPD4703	Approved
0.7035	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9726	Discontinued
0.7022	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD1032	Phase 2
0.7012	Intermediate Similarity	NPD3717	Discontinued
0.7011	Intermediate Similarity	NPD8063	Discontinued
0.6994	Remote Similarity	NPD107	Approved
0.6983	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.698	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1418	Phase 2
0.6961	Remote Similarity	NPD4086	Phase 1
0.6959	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD9271	Approved
0.6935	Remote Similarity	NPD6665	Discontinued
0.6927	Remote Similarity	NPD4071	Approved
0.6927	Remote Similarity	NPD4072	Approved
0.6914	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD425	Approved
0.6914	Remote Similarity	NPD424	Approved
0.6907	Remote Similarity	NPD1392	Approved
0.6902	Remote Similarity	NPD8021	Approved
0.6902	Remote Similarity	NPD8020	Approved
0.6878	Remote Similarity	NPD1229	Phase 2
0.6875	Remote Similarity	NPD5862	Discovery
0.6856	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2076	Approved
0.6854	Remote Similarity	NPD2077	Approved
0.6848	Remote Similarity	NPD4805	Approved
0.6845	Remote Similarity	NPD981	Phase 2
0.6836	Remote Similarity	NPD565	Phase 2
0.6824	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD9595	Approved
0.6824	Remote Similarity	NPD9596	Approved
0.6821	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD271	Approved
0.6818	Remote Similarity	NPD268	Approved
0.6818	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5065	Approved
0.6811	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD1034	Phase 3
0.6809	Remote Similarity	NPD4529	Approved
0.6809	Remote Similarity	NPD4526	Approved
0.6809	Remote Similarity	NPD4528	Approved
0.6804	Remote Similarity	NPD1915	Phase 1
0.68	Remote Similarity	NPD863	Approved
0.68	Remote Similarity	NPD861	Approved
0.68	Remote Similarity	NPD862	Approved
0.6798	Remote Similarity	NPD2123	Phase 3
0.6793	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2952	Discontinued
0.6788	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5486	Discontinued
0.6782	Remote Similarity	NPD2511	Approved
0.678	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.676	Remote Similarity	NPD1599	Approved
0.6757	Remote Similarity	NPD706	Phase 1
0.6739	Remote Similarity	NPD3569	Discontinued
0.6738	Remote Similarity	NPD3321	Discontinued
0.673	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4804	Approved
0.672	Remote Similarity	NPD4551	Phase 2
0.6718	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD8321	Discontinued
0.6714	Remote Similarity	NPD7558	Phase 2
0.6705	Remote Similarity	NPD5088	Discontinued
0.6705	Remote Similarity	NPD6026	Approved
0.6702	Remote Similarity	NPD1622	Discontinued
0.6701	Remote Similarity	NPD4612	Discontinued
0.6685	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5100	Phase 3
0.6684	Remote Similarity	NPD5458	Discontinued
0.6667	Remote Similarity	NPD925	Approved
0.6667	Remote Similarity	NPD6569	Phase 2
0.6667	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9510	Approved
0.6667	Remote Similarity	NPD2896	Discontinued
0.6667	Remote Similarity	NPD926	Approved
0.6648	Remote Similarity	NPD8026	Phase 1
0.6647	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1570	Approved
0.663	Remote Similarity	NPD8408	Discontinued
0.6625	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3525	Discontinued
0.66	Remote Similarity	NPD3570	Phase 2
0.66	Remote Similarity	NPD4131	Phase 3
0.6599	Remote Similarity	NPD7001	Phase 3
0.6593	Remote Similarity	NPD2381	Approved
0.6593	Remote Similarity	NPD2382	Approved
0.6593	Remote Similarity	NPD2380	Approved
0.6592	Remote Similarity	NPD4638	Approved
0.6592	Remote Similarity	NPD4640	Approved
0.6592	Remote Similarity	NPD4639	Approved
0.6591	Remote Similarity	NPD1741	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6529	Discontinued
0.6582	Remote Similarity	NPD9357	Approved
0.6579	Remote Similarity	NPD1234	Discontinued
0.6578	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4375	Approved
0.6568	Remote Similarity	NPD8823	Approved
0.6557	Remote Similarity	NPD8122	Approved
0.6557	Remote Similarity	NPD8123	Approved
0.6556	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5612	Discontinued
0.6552	Remote Similarity	NPD2809	Approved
0.6548	Remote Similarity	NPD4038	Approved
0.6548	Remote Similarity	NPD4035	Approved
0.6548	Remote Similarity	NPD4039	Approved
0.6548	Remote Similarity	NPD4033	Approved
0.6548	Remote Similarity	NPD31	Approved
0.6548	Remote Similarity	NPD4036	Approved
0.6548	Remote Similarity	NPD4122	Approved
0.6548	Remote Similarity	NPD4034	Approved
0.6548	Remote Similarity	NPD32	Approved
0.6548	Remote Similarity	NPD4037	Approved
0.6546	Remote Similarity	NPD1768	Approved
0.6545	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2383	Phase 1
0.6541	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3794	Approved
0.6535	Remote Similarity	NPD3795	Approved
0.6531	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6227	Discontinued
0.6519	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5067	Phase 2
0.6517	Remote Similarity	NPD5066	Phase 2
0.6515	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2876	Phase 3
0.6514	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5228	Phase 3
0.6513	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4427	Phase 2
0.6506	Remote Similarity	NPD201	Phase 2
0.6506	Remote Similarity	NPD200	Phase 2
0.6502	Remote Similarity	NPD5149	Phase 2
0.6502	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.65	Remote Similarity	NPD9583	Approved
0.6497	Remote Similarity	NPD9598	Discontinued
0.6495	Remote Similarity	NPD7778	Approved
0.6495	Remote Similarity	NPD53	Approved
0.6495	Remote Similarity	NPD7777	Approved
0.6492	Remote Similarity	NPD3404	Approved
0.6492	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD4376	Phase 3
0.6492	Remote Similarity	NPD2127	Suspended
0.6491	Remote Similarity	NPD7469	Discontinued
0.6486	Remote Similarity	NPD1618	Phase 2
0.6485	Remote Similarity	NPD3330	Phase 1
0.6484	Remote Similarity	NPD750	Phase 2
0.6482	Remote Similarity	NPD796	Phase 2

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