NPASS Compound

Structure

CID319456 OpenBabel06191716142D 22 23 0 0 1 0 0 0 0 0999 V2000 5.8916 -0.0636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2983 -0.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8970 0.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7160 -1.6817 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 5.7105 -1.7862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8366 -0.0055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8147 0.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1172 -2.6997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 -0.6636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5295 -3.5088 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3092 -0.7681 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 1.0934 0.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2215 1.1160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1118 -2.8043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 O 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 2.6456 -1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 6 1 0 0 0 0 3 13 2 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 20 1 0 0 0 0 6 10 1 0 0 0 0 7 5 1 6 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 1 0 0 0 9 11 1 0 0 0 0 9 15 1 1 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 6 0 0 0 11 21 1 0 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 19 22 2 0 0 0 0 20 22 1 0 0 0 0 M CHG 2 13 1 18 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.06
Volume:	283.296
LogP:	-2.223
LogD:	-1.377
LogS:	-0.879
# Rotatable Bonds:	5
TPSA:	163.09
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.388
Synthetic Accessibility Score:	4.968
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:	-6.102
MDCK Permeability:	0.0001523246755823493
Pgp-inhibitor:	0.0
Pgp-substrate:	0.289
Human Intestinal Absorption (HIA):	0.871
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.428
Plasma Protein Binding (PPB):	10.805339813232422%
Volume Distribution (VD):	0.421
Pgp-substrate:	92.33576965332031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	1.287
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.833
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.174
Skin Sensitization:	0.273
Carcinogencity:	0.146
Eye Corrosion:	0.003
Eye Irritation:	0.158
Respiratory Toxicity:	0.08

Download Data

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

Natural Product: NPC319456

Natural Product ID:	NPC319456
*Common Name:**	Betanmn
IUPAC Name:	[(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
Synonyms:	Beta-Nicotinamide Mononucleotide; Nicotinamide Mononucleotide
Standard InCHIKey:	DAYLJWODMCOQEW-TURQNECASA-N
Standard InCHI:	InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/t7-,8-,9-,11-/m1/s1
SMILES:	O[C@@H]1[C@H](O)[C@H](O[C@H]1[n+]1cccc(c1)C(=N)O)COP(=O)(O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL610238
PubChem CID:	14180
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0001297] Pyridine nucleotides [CHEMONTID:0001268] Nicotinamide nucleotides

*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
Ki	2
Others	1

Activity Type	# Activity
Individual Protein	4
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1224	Individual Protein	Glyceraldehyde-3-phosphate dehydrogenase liver	Homo sapiens	IC50	>	500000.0	nM	PMID[498274]
NPT1771	Individual Protein	Glutamate dehydrogenase	Bos taurus	Ki	>	10000000.0	nM	PMID[498275]
NPT3582	Individual Protein	Ketopantoate reductase	Escherichia coli K-12	Inhibition	=	0.0	%	PMID[498276]
NPT1347	Protein Family	Alcohol dehydrogenase	Equus caballus	Ki	>	10000000.0	nM	PMID[498275]

☑ 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 NPC319456 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	353
0.1-0.2	3649
0.2-0.3	13947
0.3-0.4	16679
0.4-0.5	4790
0.5-0.6	2623
0.6-0.7	630
0.7-0.8	23
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9539	High Similarity	NPC138018
0.8353	Intermediate Similarity	NPC317010
0.7895	Intermediate Similarity	NPC165370
0.7895	Intermediate Similarity	NPC306397
0.7857	Intermediate Similarity	NPC71079
0.7811	Intermediate Similarity	NPC474217
0.7778	Intermediate Similarity	NPC212125
0.7765	Intermediate Similarity	NPC85918
0.7722	Intermediate Similarity	NPC29702
0.7719	Intermediate Similarity	NPC278366
0.7719	Intermediate Similarity	NPC127730
0.7562	Intermediate Similarity	NPC107160
0.7556	Intermediate Similarity	NPC62510
0.7529	Intermediate Similarity	NPC256828
0.7516	Intermediate Similarity	NPC315320
0.7399	Intermediate Similarity	NPC211187
0.7394	Intermediate Similarity	NPC471323
0.7353	Intermediate Similarity	NPC263455
0.7263	Intermediate Similarity	NPC474767
0.7234	Intermediate Similarity	NPC20593
0.7184	Intermediate Similarity	NPC63338
0.7184	Intermediate Similarity	NPC322976
0.7184	Intermediate Similarity	NPC324203
0.7158	Intermediate Similarity	NPC325093
0.7151	Intermediate Similarity	NPC75544
0.712	Intermediate Similarity	NPC59033
0.7093	Intermediate Similarity	NPC312860
0.7081	Intermediate Similarity	NPC318020
0.7069	Intermediate Similarity	NPC132680
0.7069	Intermediate Similarity	NPC269919
0.7065	Intermediate Similarity	NPC322043
0.7065	Intermediate Similarity	NPC327373
0.7052	Intermediate Similarity	NPC63562
0.7031	Intermediate Similarity	NPC317672
0.7006	Intermediate Similarity	NPC263439
0.7006	Intermediate Similarity	NPC318935
0.7005	Intermediate Similarity	NPC328798
0.6979	Remote Similarity	NPC329024
0.697	Remote Similarity	NPC328029
0.6968	Remote Similarity	NPC182814
0.6959	Remote Similarity	NPC79223
0.6943	Remote Similarity	NPC149708
0.6941	Remote Similarity	NPC167400
0.6915	Remote Similarity	NPC325775
0.691	Remote Similarity	NPC102423
0.6906	Remote Similarity	NPC470498
0.6904	Remote Similarity	NPC12944
0.6904	Remote Similarity	NPC25442
0.6901	Remote Similarity	NPC220523
0.6897	Remote Similarity	NPC107287
0.6895	Remote Similarity	NPC127647
0.6885	Remote Similarity	NPC150048
0.6885	Remote Similarity	NPC203754
0.6875	Remote Similarity	NPC151489
0.6872	Remote Similarity	NPC471178
0.6856	Remote Similarity	NPC324245
0.6856	Remote Similarity	NPC320748
0.6851	Remote Similarity	NPC222174
0.6839	Remote Similarity	NPC292361
0.6839	Remote Similarity	NPC153769
0.6837	Remote Similarity	NPC328559
0.6837	Remote Similarity	NPC32451
0.6834	Remote Similarity	NPC156044
0.6833	Remote Similarity	NPC168702
0.6833	Remote Similarity	NPC125659
0.6829	Remote Similarity	NPC174421
0.6829	Remote Similarity	NPC324611
0.6829	Remote Similarity	NPC256893
0.6826	Remote Similarity	NPC114310
0.6816	Remote Similarity	NPC476446
0.6816	Remote Similarity	NPC469813
0.6816	Remote Similarity	NPC78375
0.681	Remote Similarity	NPC244536
0.6798	Remote Similarity	NPC131718
0.6792	Remote Similarity	NPC21461
0.6791	Remote Similarity	NPC48938
0.679	Remote Similarity	NPC471313
0.679	Remote Similarity	NPC471311
0.6784	Remote Similarity	NPC230085
0.6784	Remote Similarity	NPC159630
0.6784	Remote Similarity	NPC309498
0.678	Remote Similarity	NPC212742
0.6765	Remote Similarity	NPC313640
0.6755	Remote Similarity	NPC207851
0.674	Remote Similarity	NPC98187
0.674	Remote Similarity	NPC108469
0.6737	Remote Similarity	NPC36498
0.6736	Remote Similarity	NPC106937
0.6735	Remote Similarity	NPC160127
0.6735	Remote Similarity	NPC50997
0.6722	Remote Similarity	NPC473057
0.6721	Remote Similarity	NPC158129
0.672	Remote Similarity	NPC188387
0.672	Remote Similarity	NPC163421
0.6705	Remote Similarity	NPC161292
0.6703	Remote Similarity	NPC476419
0.6702	Remote Similarity	NPC469358
0.6687	Remote Similarity	NPC322488
0.6685	Remote Similarity	NPC313791
0.6683	Remote Similarity	NPC472752
0.6667	Remote Similarity	NPC112741
0.6667	Remote Similarity	NPC471177
0.6667	Remote Similarity	NPC124542
0.6667	Remote Similarity	NPC111732
0.6667	Remote Similarity	NPC59779
0.6649	Remote Similarity	NPC314394
0.6648	Remote Similarity	NPC230869
0.6648	Remote Similarity	NPC113812
0.6631	Remote Similarity	NPC141377
0.663	Remote Similarity	NPC273532
0.663	Remote Similarity	NPC97367
0.663	Remote Similarity	NPC162268
0.6618	Remote Similarity	NPC472285
0.6585	Remote Similarity	NPC476467
0.6585	Remote Similarity	NPC292517
0.6584	Remote Similarity	NPC316403
0.6579	Remote Similarity	NPC284559
0.6578	Remote Similarity	NPC211997
0.657	Remote Similarity	NPC288349
0.6557	Remote Similarity	NPC54988
0.6552	Remote Similarity	NPC63041
0.6538	Remote Similarity	NPC471014
0.6538	Remote Similarity	NPC311276
0.6538	Remote Similarity	NPC40779
0.6538	Remote Similarity	NPC475408
0.6524	Remote Similarity	NPC134586
0.6522	Remote Similarity	NPC265605
0.6522	Remote Similarity	NPC48564
0.6522	Remote Similarity	NPC182570
0.6507	Remote Similarity	NPC294579
0.6507	Remote Similarity	NPC144779
0.6505	Remote Similarity	NPC472553
0.6503	Remote Similarity	NPC27740
0.649	Remote Similarity	NPC477910
0.649	Remote Similarity	NPC470306
0.649	Remote Similarity	NPC30570
0.6488	Remote Similarity	NPC5145
0.6485	Remote Similarity	NPC470500
0.648	Remote Similarity	NPC289786
0.648	Remote Similarity	NPC79293
0.648	Remote Similarity	NPC279401
0.6478	Remote Similarity	NPC297486
0.6478	Remote Similarity	NPC240136
0.6478	Remote Similarity	NPC471402
0.6477	Remote Similarity	NPC46580
0.6474	Remote Similarity	NPC161887
0.6474	Remote Similarity	NPC219963
0.6474	Remote Similarity	NPC71037
0.6471	Remote Similarity	NPC76540
0.6467	Remote Similarity	NPC41717
0.6462	Remote Similarity	NPC114974
0.6459	Remote Similarity	NPC162812
0.6459	Remote Similarity	NPC6981
0.6459	Remote Similarity	NPC471016
0.6458	Remote Similarity	NPC314002
0.6458	Remote Similarity	NPC295158
0.6455	Remote Similarity	NPC133261
0.6452	Remote Similarity	NPC27802
0.6446	Remote Similarity	NPC89490
0.6443	Remote Similarity	NPC209917
0.644	Remote Similarity	NPC472110
0.644	Remote Similarity	NPC472444
0.644	Remote Similarity	NPC220765
0.644	Remote Similarity	NPC472109
0.6439	Remote Similarity	NPC304179
0.6439	Remote Similarity	NPC472550
0.6439	Remote Similarity	NPC48042
0.6436	Remote Similarity	NPC24594
0.6436	Remote Similarity	NPC472122
0.6433	Remote Similarity	NPC471312
0.6432	Remote Similarity	NPC472284
0.6432	Remote Similarity	NPC212213
0.6429	Remote Similarity	NPC471322
0.6429	Remote Similarity	NPC314270
0.6425	Remote Similarity	NPC171171
0.6425	Remote Similarity	NPC315555
0.6421	Remote Similarity	NPC325705
0.6421	Remote Similarity	NPC52831
0.6419	Remote Similarity	NPC476492
0.6413	Remote Similarity	NPC477975
0.6413	Remote Similarity	NPC41333
0.641	Remote Similarity	NPC95783
0.6409	Remote Similarity	NPC469762
0.6409	Remote Similarity	NPC129721
0.6407	Remote Similarity	NPC329896
0.6407	Remote Similarity	NPC475090
0.6407	Remote Similarity	NPC475105
0.6406	Remote Similarity	NPC284678
0.6406	Remote Similarity	NPC204717
0.6402	Remote Similarity	NPC326575
0.6402	Remote Similarity	NPC475498
0.6402	Remote Similarity	NPC475137
0.6402	Remote Similarity	NPC96890
0.6402	Remote Similarity	NPC184964
0.6398	Remote Similarity	NPC472555
0.6398	Remote Similarity	NPC313804
0.6398	Remote Similarity	NPC315804
0.6398	Remote Similarity	NPC84815
0.6398	Remote Similarity	NPC250178
0.6398	Remote Similarity	NPC216428

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 NPC319456 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	637
0.2-0.3	942
0.3-0.4	1917
0.4-0.5	3353
0.5-0.6	1821
0.6-0.7	305
0.7-0.8	17
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD2544	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD9506	Approved
0.7895	Intermediate Similarity	NPD9080	Approved
0.7778	Intermediate Similarity	NPD9284	Approved
0.7625	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD9206	Approved
0.7516	Intermediate Similarity	NPD9207	Approved
0.7423	Intermediate Similarity	NPD1649	Discontinued
0.7394	Intermediate Similarity	NPD1352	Discontinued
0.7374	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1380	Discovery
0.7186	Intermediate Similarity	NPD3813	Approved
0.7184	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1382	Phase 2
0.7169	Intermediate Similarity	NPD1383	Phase 3
0.7126	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD9382	Approved
0.7069	Intermediate Similarity	NPD9383	Approved
0.6971	Remote Similarity	NPD820	Phase 3
0.6941	Remote Similarity	NPD9075	Approved
0.6941	Remote Similarity	NPD9074	Approved
0.6936	Remote Similarity	NPD510	Phase 1
0.6935	Remote Similarity	NPD1096	Discontinued
0.6932	Remote Similarity	NPD5255	Approved
0.6919	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7396	Approved
0.6898	Remote Similarity	NPD3082	Discontinued
0.6895	Remote Similarity	NPD4699	Discontinued
0.6878	Remote Similarity	NPD4021	Phase 2
0.6875	Remote Similarity	NPD2582	Approved
0.6875	Remote Similarity	NPD2581	Approved
0.6859	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4086	Phase 1
0.6791	Remote Similarity	NPD5596	Phase 2
0.6786	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4703	Approved
0.6763	Remote Similarity	NPD4702	Approved
0.676	Remote Similarity	NPD4239	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1032	Phase 2
0.6757	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD8063	Discontinued
0.6737	Remote Similarity	NPD9363	Approved
0.6737	Remote Similarity	NPD9364	Phase 2
0.6736	Remote Similarity	NPD802	Phase 2
0.6727	Remote Similarity	NPD9726	Discontinued
0.6725	Remote Similarity	NPD3717	Discontinued
0.672	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD107	Approved
0.6704	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD1418	Phase 2
0.6685	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6665	Discontinued
0.6667	Remote Similarity	NPD4072	Approved
0.6667	Remote Similarity	NPD4071	Approved
0.6667	Remote Similarity	NPD5316	Approved
0.6667	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9271	Approved
0.6667	Remote Similarity	NPD1392	Approved
0.6649	Remote Similarity	NPD8021	Approved
0.6649	Remote Similarity	NPD9362	Approved
0.6649	Remote Similarity	NPD8020	Approved
0.6648	Remote Similarity	NPD424	Approved
0.6648	Remote Similarity	NPD425	Approved
0.6648	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD1229	Phase 2
0.663	Remote Similarity	NPD8129	Discovery
0.6617	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5862	Discovery
0.6598	Remote Similarity	NPD981	Phase 2
0.6595	Remote Similarity	NPD2076	Approved
0.6595	Remote Similarity	NPD2077	Approved
0.6592	Remote Similarity	NPD6351	Discovery
0.6576	Remote Similarity	NPD565	Phase 2
0.657	Remote Similarity	NPD4805	Approved
0.6569	Remote Similarity	NPD8321	Discontinued
0.6567	Remote Similarity	NPD1915	Phase 1
0.6564	Remote Similarity	NPD4526	Approved
0.6564	Remote Similarity	NPD4528	Approved
0.6564	Remote Similarity	NPD4529	Approved
0.6562	Remote Similarity	NPD1034	Phase 3
0.6562	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5065	Approved
0.6556	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD9596	Approved
0.6554	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD9595	Approved
0.655	Remote Similarity	NPD5486	Discontinued
0.6548	Remote Similarity	NPD2952	Discontinued
0.6545	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2123	Phase 3
0.6538	Remote Similarity	NPD861	Approved
0.6538	Remote Similarity	NPD863	Approved
0.6538	Remote Similarity	NPD862	Approved
0.6528	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD268	Approved
0.6522	Remote Similarity	NPD271	Approved
0.6522	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2511	Approved
0.6512	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.651	Remote Similarity	NPD706	Phase 1
0.6505	Remote Similarity	NPD1599	Approved
0.65	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD7558	Phase 2
0.6497	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3321	Discontinued
0.6492	Remote Similarity	NPD3569	Discontinued
0.6485	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4551	Phase 2
0.6471	Remote Similarity	NPD4612	Discontinued
0.6465	Remote Similarity	NPD1622	Discontinued
0.6453	Remote Similarity	NPD5458	Discontinued
0.6453	Remote Similarity	NPD4804	Approved
0.6448	Remote Similarity	NPD5088	Discontinued
0.6446	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6026	Approved
0.6439	Remote Similarity	NPD6529	Discontinued
0.6436	Remote Similarity	NPD5100	Phase 3
0.6432	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD9582	Phase 3
0.6429	Remote Similarity	NPD6569	Phase 2
0.6421	Remote Similarity	NPD9510	Approved
0.6413	Remote Similarity	NPD926	Approved
0.6413	Remote Similarity	NPD925	Approved
0.64	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2896	Discontinued
0.6393	Remote Similarity	NPD8026	Phase 1
0.6387	Remote Similarity	NPD1570	Approved
0.6387	Remote Similarity	NPD8408	Discontinued
0.6384	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD3570	Phase 2
0.6377	Remote Similarity	NPD4131	Phase 3
0.6373	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7001	Phase 3
0.6349	Remote Similarity	NPD2381	Approved
0.6349	Remote Similarity	NPD2382	Approved
0.6349	Remote Similarity	NPD2380	Approved
0.6347	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD1234	Discontinued
0.6344	Remote Similarity	NPD4638	Approved
0.6344	Remote Similarity	NPD4639	Approved
0.6344	Remote Similarity	NPD4640	Approved
0.6343	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD3525	Discontinued
0.634	Remote Similarity	NPD1063	Phase 2
0.634	Remote Similarity	NPD4375	Approved
0.634	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD1741	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5612	Discontinued
0.6328	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD4036	Approved
0.6324	Remote Similarity	NPD4037	Approved
0.6324	Remote Similarity	NPD4034	Approved
0.6324	Remote Similarity	NPD4038	Approved
0.6324	Remote Similarity	NPD32	Approved
0.6324	Remote Similarity	NPD4035	Approved
0.6324	Remote Similarity	NPD4122	Approved
0.6324	Remote Similarity	NPD4039	Approved
0.6324	Remote Similarity	NPD31	Approved
0.6324	Remote Similarity	NPD4033	Approved
0.6318	Remote Similarity	NPD1768	Approved
0.6316	Remote Similarity	NPD8123	Approved
0.6316	Remote Similarity	NPD3795	Approved
0.6316	Remote Similarity	NPD3794	Approved
0.6316	Remote Similarity	NPD8122	Approved
0.631	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD2383	Phase 1
0.6307	Remote Similarity	NPD8823	Approved
0.6305	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD9357	Approved
0.6302	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD5066	Phase 2
0.6298	Remote Similarity	NPD2809	Approved
0.6298	Remote Similarity	NPD5067	Phase 2
0.6296	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD2876	Phase 3
0.6289	Remote Similarity	NPD6227	Discontinued
0.6287	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD5228	Phase 3
0.6286	Remote Similarity	NPD5149	Phase 2
0.6286	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD4427	Phase 2
0.6279	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7778	Approved
0.6269	Remote Similarity	NPD7777	Approved
0.6269	Remote Similarity	NPD53	Approved
0.6268	Remote Similarity	NPD3330	Phase 1
0.6264	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD3404	Approved
0.6263	Remote Similarity	NPD4376	Phase 3

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