NPASS Compound

Structure

CID321814 OpenBabel06191716162D 23 25 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1694 -3.3283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9784 -0.0250 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 5.7874 -1.4262 0.0000 C 0 0 0 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 6.4565 -2.1694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8092 -1.6341 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 7.4347 -1.9615 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1475 -3.1204 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5002 -2.5852 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8919 -0.4317 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3092 -0.7681 0.0000 N 0 0 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 0.0000 1.0000 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 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 21 1 0 0 0 0 2 13 2 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 3 16 1 0 0 0 0 4 1 1 6 0 0 0 4 6 1 0 0 0 0 4 22 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 1 0 0 0 7 10 1 0 0 0 0 7 18 1 1 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 16 1 6 0 0 0 10 22 1 0 0 0 0 12 23 1 0 0 0 0 19 23 1 0 0 0 0 20 23 2 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.08
Volume:	283.85
LogP:	-2.762
LogD:	-1.526
LogS:	-0.788
# Rotatable Bonds:	4
TPSA:	189.43
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.394
Synthetic Accessibility Score:	5.146
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.214
MDCK Permeability:	7.588643256895011e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.981
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.562
Plasma Protein Binding (PPB):	13.278434753417969%
Volume Distribution (VD):	0.757
Pgp-substrate:	85.55261993408203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.64
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.024

ADMET: Excretion

Clearance (CL):	1.456
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.85
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.386
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.421
Carcinogencity:	0.213
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC321814

Natural Product ID:	NPC321814
*Common Name:**	Adenosine-5'-Phosphoramidate
IUPAC Name:	[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonamidic acid
Synonyms:
Standard InCHIKey:	LDEMREUBLBGZBO-KQYNXXCUSA-N
Standard InCHI:	InChI=1S/C10H15N6O6P/c11-8-5-9(14-2-13-8)16(3-15-5)10-7(18)6(17)4(22-10)1-21-23(12,19)20/h2-4,6-7,10,17-18H,1H2,(H2,11,13,14)(H3,12,19,20)/t4-,6-,7-,10-/m1/s1
SMILES:	O[C@@H]1[C@H](O)[C@H](O[C@H]1n1cnc2c1ncnc2N)COP(=O)(O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL583986
PubChem CID:	440142
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0001506] Purine nucleotides [CHEMONTID:0001544] Purine ribonucleotides [CHEMONTID:0001617] Purine ribonucleoside monophosphates

*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
NPO30193	Mycoplasma genitalium	Species	Mycoplasmataceae	Bacteria	n.a.	n.a.	n.a.	PMID[22817898]

☑ 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
Kd	5
Ki	2
Others	3

Activity Type	# Activity
Individual Protein	6
Others	3
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4504	Individual Protein	Endoplasmin	Homo sapiens	Kd	>	50000.0	nM	PMID[553477]
NPT4504	Individual Protein	Endoplasmin	Homo sapiens	Ki	>	10000.0	nM	PMID[553477]
NPT4504	Individual Protein	Endoplasmin	Homo sapiens	Activity	=	10.0	%	PMID[553477]
NPT2	Others	Unspecified		Kd	=	100000.0	nM	PMID[553474]
NPT2	Others	Unspecified		Kd	=	82000.0	nM	PMID[553474]
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	Kd	>	50000.0	nM	PMID[553477]
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	Ki	>	3000.0	nM	PMID[553477]
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	Activity	=	9.0	%	PMID[553477]
NPT27874	SINGLE PROTEIN	Histidine triad nucleotide-binding protein 1	Oryctolagus cuniculus	Drug metabolism	=	1.71	nmol/min	PMID[553476]

☑ 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 NPC321814 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	981
0.1-0.2	30365
0.2-0.3	7057
0.3-0.4	3486
0.4-0.5	508
0.5-0.6	130
0.6-0.7	64
0.7-0.8	31
0.8-0.85	21
0.85-0.9	24
0.9-0.95	17
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC85689
0.9928	High Similarity	NPC211025
0.9928	High Similarity	NPC185991
0.9787	High Similarity	NPC212551
0.9787	High Similarity	NPC164952
0.9787	High Similarity	NPC130586
0.9787	High Similarity	NPC302778
0.9718	High Similarity	NPC174802
0.9712	High Similarity	NPC121222
0.965	High Similarity	NPC224076
0.9583	High Similarity	NPC226245
0.9583	High Similarity	NPC316618
0.9507	High Similarity	NPC161224
0.9496	High Similarity	NPC156461
0.9496	High Similarity	NPC107374
0.9496	High Similarity	NPC21448
0.9429	High Similarity	NPC189068
0.9429	High Similarity	NPC164665
0.9362	High Similarity	NPC269827
0.9362	High Similarity	NPC309832
0.9362	High Similarity	NPC219313
0.9353	High Similarity	NPC229974
0.9262	High Similarity	NPC323091
0.9209	High Similarity	NPC161659
0.9209	High Similarity	NPC209525
0.9078	High Similarity	NPC314152
0.9071	High Similarity	NPC317821
0.9041	High Similarity	NPC472816
0.8889	High Similarity	NPC261595
0.8831	High Similarity	NPC321458
0.8831	High Similarity	NPC324033
0.88	High Similarity	NPC239737
0.879	High Similarity	NPC326529
0.8784	High Similarity	NPC207633
0.8734	High Similarity	NPC319100
0.8734	High Similarity	NPC189261
0.8734	High Similarity	NPC324198
0.8732	High Similarity	NPC129756
0.8654	High Similarity	NPC326082
0.8649	High Similarity	NPC150853
0.8581	High Similarity	NPC136349
0.8553	High Similarity	NPC54320
0.8553	High Similarity	NPC313754
0.8553	High Similarity	NPC311197
0.8487	Intermediate Similarity	NPC52238
0.8411	Intermediate Similarity	NPC328479
0.8403	Intermediate Similarity	NPC33996
0.8403	Intermediate Similarity	NPC30326
0.8392	Intermediate Similarity	NPC320818
0.8311	Intermediate Similarity	NPC274384
0.8311	Intermediate Similarity	NPC89147
0.8243	Intermediate Similarity	NPC211820
0.8243	Intermediate Similarity	NPC251233
0.8231	Intermediate Similarity	NPC186619
0.8188	Intermediate Similarity	NPC177169
0.8141	Intermediate Similarity	NPC195140
0.8133	Intermediate Similarity	NPC64705
0.8133	Intermediate Similarity	NPC232408
0.8121	Intermediate Similarity	NPC318590
0.8077	Intermediate Similarity	NPC93365
0.8067	Intermediate Similarity	NPC317746
0.8039	Intermediate Similarity	NPC326694
0.8	Intermediate Similarity	NPC324484
0.7963	Intermediate Similarity	NPC290959
0.795	Intermediate Similarity	NPC325906
0.7891	Intermediate Similarity	NPC61198
0.7823	Intermediate Similarity	NPC262926
0.7707	Intermediate Similarity	NPC321052
0.7665	Intermediate Similarity	NPC313897
0.7654	Intermediate Similarity	NPC14590
0.7635	Intermediate Similarity	NPC319221
0.7568	Intermediate Similarity	NPC324009
0.7457	Intermediate Similarity	NPC24589
0.7429	Intermediate Similarity	NPC78941
0.7429	Intermediate Similarity	NPC282458
0.7355	Intermediate Similarity	NPC315642
0.7355	Intermediate Similarity	NPC74306
0.7232	Intermediate Similarity	NPC313514
0.7202	Intermediate Similarity	NPC33382
0.716	Intermediate Similarity	NPC125659
0.716	Intermediate Similarity	NPC168702
0.7076	Intermediate Similarity	NPC222174
0.6964	Remote Similarity	NPC321393
0.6952	Remote Similarity	NPC276373
0.6915	Remote Similarity	NPC5802
0.6878	Remote Similarity	NPC157821
0.6871	Remote Similarity	NPC327579
0.6832	Remote Similarity	NPC107160
0.6732	Remote Similarity	NPC21461
0.6667	Remote Similarity	NPC476564
0.6667	Remote Similarity	NPC57279
0.6645	Remote Similarity	NPC104011
0.6645	Remote Similarity	NPC246193
0.6635	Remote Similarity	NPC158055
0.6571	Remote Similarity	NPC87981
0.6571	Remote Similarity	NPC174114
0.6567	Remote Similarity	NPC250178
0.6536	Remote Similarity	NPC248007
0.6438	Remote Similarity	NPC312187
0.6438	Remote Similarity	NPC4837
0.6359	Remote Similarity	NPC103388
0.634	Remote Similarity	NPC139776
0.6329	Remote Similarity	NPC287876
0.6266	Remote Similarity	NPC14330
0.6256	Remote Similarity	NPC160666
0.6207	Remote Similarity	NPC18335
0.6185	Remote Similarity	NPC472834
0.6051	Remote Similarity	NPC109322
0.5974	Remote Similarity	NPC68938
0.5914	Remote Similarity	NPC164845
0.5886	Remote Similarity	NPC5707
0.5882	Remote Similarity	NPC313547
0.5882	Remote Similarity	NPC217656
0.5848	Remote Similarity	NPC89139
0.5833	Remote Similarity	NPC296437
0.5813	Remote Similarity	NPC180493
0.5799	Remote Similarity	NPC470266
0.5769	Remote Similarity	NPC189314
0.5747	Remote Similarity	NPC244700
0.5743	Remote Similarity	NPC476561
0.5731	Remote Similarity	NPC476528
0.5731	Remote Similarity	NPC476433
0.5699	Remote Similarity	NPC265111
0.5698	Remote Similarity	NPC474986
0.5698	Remote Similarity	NPC476013
0.5698	Remote Similarity	NPC476522
0.5698	Remote Similarity	NPC476520
0.5698	Remote Similarity	NPC472833
0.569	Remote Similarity	NPC476408
0.5665	Remote Similarity	NPC476521
0.5654	Remote Similarity	NPC473585
0.5629	Remote Similarity	NPC119133
0.5604	Remote Similarity	NPC472832
0.5604	Remote Similarity	NPC18308

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 NPC321814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	2423
0.2-0.3	3187
0.3-0.4	2141
0.4-0.5	844
0.5-0.6	145
0.6-0.7	131
0.7-0.8	42
0.8-0.85	21
0.85-0.9	13
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9928	High Similarity	NPD283	Approved
0.9787	High Similarity	NPD242	Approved
0.9787	High Similarity	NPD338	Approved
0.9718	High Similarity	NPD339	Approved
0.965	High Similarity	NPD169	Phase 2
0.9496	High Similarity	NPD250	Approved
0.9496	High Similarity	NPD249	Approved
0.9362	High Similarity	NPD186	Discovery
0.9362	High Similarity	NPD195	Approved
0.9078	High Similarity	NPD185	Approved
0.898	High Similarity	NPD3107	Discontinued
0.898	High Similarity	NPD1369	Phase 2
0.898	High Similarity	NPD1750	Clinical (unspecified phase)
0.8951	High Similarity	NPD166	Approved
0.8936	High Similarity	NPD193	Suspended
0.8889	High Similarity	NPD247	Clinical (unspecified phase)
0.88	High Similarity	NPD2624	Phase 2
0.88	High Similarity	NPD1732	Phase 3
0.88	High Similarity	NPD2646	Discontinued
0.8766	High Similarity	NPD7988	Suspended
0.8734	High Similarity	NPD4171	Clinical (unspecified phase)
0.8679	High Similarity	NPD1412	Clinical (unspecified phase)
0.8581	High Similarity	NPD548	Clinical (unspecified phase)
0.8571	High Similarity	NPD3083	Approved
0.8571	High Similarity	NPD4716	Approved
0.8553	High Similarity	NPD217	Approved
0.8553	High Similarity	NPD216	Approved
0.8553	High Similarity	NPD219	Phase 3
0.8553	High Similarity	NPD220	Clinical (unspecified phase)
0.8553	High Similarity	NPD218	Approved
0.8519	High Similarity	NPD4744	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD214	Approved
0.8355	Intermediate Similarity	NPD213	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD2647	Phase 3
0.8313	Intermediate Similarity	NPD6417	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD2631	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD2632	Approved
0.8214	Intermediate Similarity	NPD2630	Approved
0.8169	Intermediate Similarity	NPD248	Discontinued
0.8099	Intermediate Similarity	NPD9633	Phase 3
0.8098	Intermediate Similarity	NPD5666	Phase 2
0.8077	Intermediate Similarity	NPD546	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD7158	Phase 1
0.8042	Intermediate Similarity	NPD9632	Phase 3
0.8014	Intermediate Similarity	NPD9408	Phase 3
0.795	Intermediate Similarity	NPD1777	Approved
0.795	Intermediate Similarity	NPD1776	Approved
0.7902	Intermediate Similarity	NPD870	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD252	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3085	Phase 1
0.7799	Intermediate Similarity	NPD4074	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD1692	Approved
0.7756	Intermediate Similarity	NPD3086	Phase 3
0.7702	Intermediate Similarity	NPD516	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD549	Approved
0.7674	Intermediate Similarity	NPD5684	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5682	Phase 3
0.7674	Intermediate Similarity	NPD5683	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD194	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3695	Approved
0.7566	Intermediate Similarity	NPD3696	Approved
0.7543	Intermediate Similarity	NPD4054	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD536	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD582	Approved
0.7261	Intermediate Similarity	NPD171	Discontinued
0.725	Intermediate Similarity	NPD3708	Phase 2
0.7232	Intermediate Similarity	NPD7138	Phase 2
0.7205	Intermediate Similarity	NPD353	Discontinued
0.7197	Intermediate Similarity	NPD4240	Approved
0.7175	Intermediate Similarity	NPD1063	Phase 2
0.7055	Intermediate Similarity	NPD231	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2965	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2876	Phase 3
0.6984	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD9605	Phase 3
0.6918	Remote Similarity	NPD9606	Approved
0.6911	Remote Similarity	NPD2824	Phase 2
0.6888	Remote Similarity	NPD5080	Phase 2
0.6871	Remote Similarity	NPD9607	Approved
0.6837	Remote Similarity	NPD5079	Phase 2
0.6836	Remote Similarity	NPD1046	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD2902	Phase 2
0.6731	Remote Similarity	NPD209	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD9409	Discontinued
0.6667	Remote Similarity	NPD545	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4495	Phase 1
0.6635	Remote Similarity	NPD6840	Approved
0.6599	Remote Similarity	NPD9374	Approved
0.659	Remote Similarity	NPD527	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1730	Discontinued
0.6575	Remote Similarity	NPD9373	Approved
0.6561	Remote Similarity	NPD547	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD9084	Phase 2
0.6533	Remote Similarity	NPD307	Approved
0.6497	Remote Similarity	NPD282	Approved
0.6478	Remote Similarity	NPD1119	Phase 2
0.6407	Remote Similarity	NPD775	Approved
0.6364	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD1430	Approved
0.6341	Remote Similarity	NPD1431	Approved
0.6341	Remote Similarity	NPD2253	Discontinued
0.6329	Remote Similarity	NPD8829	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD1058	Discontinued
0.6312	Remote Similarity	NPD9083	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD207	Discontinued
0.6267	Remote Similarity	NPD9584	Phase 2
0.6256	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD4458	Phase 2
0.625	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8836	Approved
0.6203	Remote Similarity	NPD1127	Approved
0.6203	Remote Similarity	NPD1128	Approved
0.6178	Remote Similarity	NPD281	Approved
0.6159	Remote Similarity	NPD1808	Phase 1
0.6159	Remote Similarity	NPD799	Phase 1
0.6106	Remote Similarity	NPD6381	Phase 2
0.6098	Remote Similarity	NPD6112	Approved
0.6084	Remote Similarity	NPD1118	Discontinued
0.6081	Remote Similarity	NPD9416	Phase 3
0.6081	Remote Similarity	NPD9417	Phase 3
0.6067	Remote Similarity	NPD9375	Discontinued
0.6051	Remote Similarity	NPD798	Discontinued
0.6037	Remote Similarity	NPD1120	Approved
0.6037	Remote Similarity	NPD1121	Approved
0.6037	Remote Similarity	NPD535	Approved
0.603	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.603	Remote Similarity	NPD4714	Approved
0.603	Remote Similarity	NPD34	Approved
0.603	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD9626	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5486	Discontinued
0.5978	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD9484	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD515	Phase 1
0.5917	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD1816	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD9582	Phase 3
0.5893	Remote Similarity	NPD8250	Phase 2
0.5891	Remote Similarity	NPD5458	Discontinued
0.5888	Remote Similarity	NPD691	Discontinued
0.5886	Remote Similarity	NPD8830	Phase 3
0.5862	Remote Similarity	NPD2452	Phase 2
0.5862	Remote Similarity	NPD2453	Phase 2
0.5862	Remote Similarity	NPD2451	Phase 2
0.5862	Remote Similarity	NPD2450	Phase 2
0.5849	Remote Similarity	NPD6036	Suspended
0.5844	Remote Similarity	NPD9406	Approved
0.5829	Remote Similarity	NPD7842	Phase 2
0.5813	Remote Similarity	NPD9544	Approved
0.5813	Remote Similarity	NPD78	Approved
0.5784	Remote Similarity	NPD796	Phase 2
0.5769	Remote Similarity	NPD8833	Approved
0.5769	Remote Similarity	NPD8831	Approved
0.5742	Remote Similarity	NPD757	Phase 3
0.5732	Remote Similarity	NPD9360	Approved
0.5708	Remote Similarity	NPD537	Phase 2
0.5708	Remote Similarity	NPD534	Phase 2
0.5708	Remote Similarity	NPD5627	Approved
0.5672	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD1368	Approved
0.5658	Remote Similarity	NPD6351	Discovery
0.565	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD1775	Approved
0.5644	Remote Similarity	NPD1085	Approved
0.5634	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.5633	Remote Similarity	NPD237	Clinical (unspecified phase)
0.5629	Remote Similarity	NPD9291	Approved
0.5628	Remote Similarity	NPD5768	Phase 2
0.5625	Remote Similarity	NPD2221	Clinical (unspecified phase)
0.5611	Remote Similarity	NPD1017	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD9704	Approved
0.5602	Remote Similarity	NPD9650	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