NPASS Compound

Structure

CID325651 OpenBabel06191716182D 25 26 0 0 1 0 0 0 0 0999 V2000 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 11 2 0 0 0 0 2 6 2 0 0 0 0 2 11 1 0 0 0 0 3 7 1 0 0 0 0 3 12 2 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 6 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 20 2 3 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.14
Volume:	347.624
LogP:	-0.164
LogD:	0.058
LogS:	-2.339
# Rotatable Bonds:	8
TPSA:	132.88
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.504
Synthetic Accessibility Score:	2.637
Fsp3:	0.222
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:	-6.235
MDCK Permeability:	2.1123883925611153e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.052
Human Intestinal Absorption (HIA):	0.17
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	49.37175750732422%
Volume Distribution (VD):	0.269
Pgp-substrate:	59.25333023071289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.465
CYP3A4-inhibitor:	0.298
CYP3A4-substrate:	0.065

ADMET: Excretion

Clearance (CL):	15.331
Half-life (T1/2):	0.919

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.343
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.15
Carcinogencity:	0.191
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC325651

Natural Product ID:	NPC325651
*Common Name:**	Tyr-Tyr
IUPAC Name:	(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
Synonyms:	Tyr-Tyr
Standard InCHIKey:	JAQGKXUEKGKTKX-HOTGVXAUSA-N
Standard InCHI:	InChI=1S/C18H20N2O5/c19-15(9-11-1-5-13(21)6-2-11)17(23)20-16(18(24)25)10-12-3-7-14(22)8-4-12/h1-8,15-16,21-22H,9-10,19H2,(H,20,23)(H,24,25)/t15-,16-/m0/s1
SMILES:	Oc1ccc(cc1)C[C@@H](C(=O)O)N=C([C@H](Cc1ccc(cc1)O)N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL95286
PubChem CID:	70590 6998943
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides

*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
EC50	1
IC50	2
Others	2

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5472	Individual Protein	Tyrosyl-tRNA synthetase	Homo sapiens	IC50	=	3800.0	nM	PMID[493167]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	EC50	=	60000.0	nM	PMID[493168]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	max activation	=	69.0	%	PMID[493168]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	IC50	=	60000.0	nM	PMID[493168]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	Ratio	=	1200.0	n.a.	PMID[493168]

☑ 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 NPC325651 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	163
0.1-0.2	1291
0.2-0.3	5677
0.3-0.4	11495
0.4-0.5	8840
0.5-0.6	12629
0.6-0.7	2194
0.7-0.8	338
0.8-0.85	50
0.85-0.9	13
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.952	High Similarity	NPC326966
0.9421	High Similarity	NPC27581
0.9141	High Similarity	NPC244866
0.9016	High Similarity	NPC319950
0.8926	High Similarity	NPC106551
0.8926	High Similarity	NPC188867
0.8926	High Similarity	NPC281686
0.8769	High Similarity	NPC45191
0.876	High Similarity	NPC478147
0.871	High Similarity	NPC239697
0.8682	High Similarity	NPC296712
0.8651	High Similarity	NPC142577
0.8647	High Similarity	NPC6913
0.856	High Similarity	NPC283760
0.8548	High Similarity	NPC38458
0.8548	High Similarity	NPC311737
0.8519	High Similarity	NPC48202
0.8504	High Similarity	NPC474862
0.848	Intermediate Similarity	NPC317784
0.848	Intermediate Similarity	NPC142638
0.8468	Intermediate Similarity	NPC82963
0.8462	Intermediate Similarity	NPC476353
0.843	Intermediate Similarity	NPC319579
0.8425	Intermediate Similarity	NPC326079
0.8288	Intermediate Similarity	NPC469243
0.8261	Intermediate Similarity	NPC91953
0.8258	Intermediate Similarity	NPC161593
0.8258	Intermediate Similarity	NPC16031
0.8258	Intermediate Similarity	NPC145888
0.824	Intermediate Similarity	NPC317254
0.8235	Intermediate Similarity	NPC6570
0.8188	Intermediate Similarity	NPC197921
0.8163	Intermediate Similarity	NPC475544
0.816	Intermediate Similarity	NPC118202
0.8148	Intermediate Similarity	NPC470392
0.8129	Intermediate Similarity	NPC469360
0.8121	Intermediate Similarity	NPC223207
0.8115	Intermediate Similarity	NPC24101
0.8115	Intermediate Similarity	NPC96224
0.8088	Intermediate Similarity	NPC267237
0.808	Intermediate Similarity	NPC309808
0.8067	Intermediate Similarity	NPC304074
0.8067	Intermediate Similarity	NPC471771
0.8067	Intermediate Similarity	NPC290755
0.8058	Intermediate Similarity	NPC259800
0.8058	Intermediate Similarity	NPC241086
0.8058	Intermediate Similarity	NPC328137
0.8058	Intermediate Similarity	NPC318984
0.8058	Intermediate Similarity	NPC282087
0.8058	Intermediate Similarity	NPC317741
0.8058	Intermediate Similarity	NPC318028
0.803	Intermediate Similarity	NPC4974
0.8028	Intermediate Similarity	NPC16188
0.8015	Intermediate Similarity	NPC88667
0.8014	Intermediate Similarity	NPC473580
0.8	Intermediate Similarity	NPC474584
0.8	Intermediate Similarity	NPC63931
0.7967	Intermediate Similarity	NPC153690
0.7951	Intermediate Similarity	NPC231705
0.7941	Intermediate Similarity	NPC257390
0.7941	Intermediate Similarity	NPC48909
0.7929	Intermediate Similarity	NPC326860
0.7929	Intermediate Similarity	NPC197239
0.792	Intermediate Similarity	NPC329011
0.7914	Intermediate Similarity	NPC313694
0.7914	Intermediate Similarity	NPC242159
0.7908	Intermediate Similarity	NPC274198
0.7908	Intermediate Similarity	NPC198254
0.7905	Intermediate Similarity	NPC56635
0.7903	Intermediate Similarity	NPC258056
0.7883	Intermediate Similarity	NPC328070
0.7879	Intermediate Similarity	NPC35996
0.7863	Intermediate Similarity	NPC56634
0.7857	Intermediate Similarity	NPC214988
0.7851	Intermediate Similarity	NPC164859
0.7847	Intermediate Similarity	NPC17760
0.7846	Intermediate Similarity	NPC268572
0.784	Intermediate Similarity	NPC474149
0.781	Intermediate Similarity	NPC275538
0.7808	Intermediate Similarity	NPC233702
0.7805	Intermediate Similarity	NPC327481
0.7793	Intermediate Similarity	NPC132771
0.7792	Intermediate Similarity	NPC276506
0.7786	Intermediate Similarity	NPC473052
0.7786	Intermediate Similarity	NPC473055
0.7778	Intermediate Similarity	NPC199738
0.7778	Intermediate Similarity	NPC321561
0.7778	Intermediate Similarity	NPC210950
0.7755	Intermediate Similarity	NPC202198
0.7746	Intermediate Similarity	NPC168861
0.7742	Intermediate Similarity	NPC142297
0.773	Intermediate Similarity	NPC322526
0.7712	Intermediate Similarity	NPC61004
0.7708	Intermediate Similarity	NPC81026
0.7707	Intermediate Similarity	NPC196243
0.7705	Intermediate Similarity	NPC178902
0.7676	Intermediate Similarity	NPC476989
0.7674	Intermediate Similarity	NPC197470
0.7664	Intermediate Similarity	NPC271808
0.7662	Intermediate Similarity	NPC328649
0.7661	Intermediate Similarity	NPC70843
0.7661	Intermediate Similarity	NPC188677
0.7642	Intermediate Similarity	NPC120693
0.7642	Intermediate Similarity	NPC261573
0.7642	Intermediate Similarity	NPC8931
0.7639	Intermediate Similarity	NPC266741
0.7638	Intermediate Similarity	NPC227553
0.7638	Intermediate Similarity	NPC163674
0.7634	Intermediate Similarity	NPC122009
0.7632	Intermediate Similarity	NPC241794
0.7628	Intermediate Similarity	NPC89831
0.7606	Intermediate Similarity	NPC471201
0.7603	Intermediate Similarity	NPC245561
0.7603	Intermediate Similarity	NPC125732
0.758	Intermediate Similarity	NPC306804
0.7574	Intermediate Similarity	NPC477937
0.7569	Intermediate Similarity	NPC66518
0.7562	Intermediate Similarity	NPC153554
0.7557	Intermediate Similarity	NPC283468
0.7548	Intermediate Similarity	NPC209463
0.7541	Intermediate Similarity	NPC52472
0.7534	Intermediate Similarity	NPC119569
0.7521	Intermediate Similarity	NPC107619
0.752	Intermediate Similarity	NPC95178
0.752	Intermediate Similarity	NPC69332
0.752	Intermediate Similarity	NPC29989
0.7518	Intermediate Similarity	NPC470441
0.75	Intermediate Similarity	NPC280022
0.75	Intermediate Similarity	NPC314992
0.75	Intermediate Similarity	NPC47667
0.75	Intermediate Similarity	NPC319320
0.75	Intermediate Similarity	NPC287757
0.7482	Intermediate Similarity	NPC474091
0.748	Intermediate Similarity	NPC88141
0.748	Intermediate Similarity	NPC145638
0.748	Intermediate Similarity	NPC290566
0.7467	Intermediate Similarity	NPC39431
0.7466	Intermediate Similarity	NPC473804
0.7459	Intermediate Similarity	NPC12730
0.7452	Intermediate Similarity	NPC46009
0.7448	Intermediate Similarity	NPC13696
0.7444	Intermediate Similarity	NPC43275
0.744	Intermediate Similarity	NPC13495
0.7438	Intermediate Similarity	NPC293628
0.7438	Intermediate Similarity	NPC122493
0.7438	Intermediate Similarity	NPC10781
0.7434	Intermediate Similarity	NPC207675
0.7434	Intermediate Similarity	NPC212699
0.7417	Intermediate Similarity	NPC476268
0.7402	Intermediate Similarity	NPC31274
0.74	Intermediate Similarity	NPC56685
0.7391	Intermediate Similarity	NPC194671
0.7391	Intermediate Similarity	NPC269750
0.7388	Intermediate Similarity	NPC190663
0.7383	Intermediate Similarity	NPC473491
0.7383	Intermediate Similarity	NPC324081
0.7364	Intermediate Similarity	NPC177576
0.7358	Intermediate Similarity	NPC475532
0.7358	Intermediate Similarity	NPC273755
0.7358	Intermediate Similarity	NPC137627
0.7358	Intermediate Similarity	NPC248670
0.7357	Intermediate Similarity	NPC120251
0.7348	Intermediate Similarity	NPC2265
0.7348	Intermediate Similarity	NPC128249
0.7343	Intermediate Similarity	NPC64205
0.7333	Intermediate Similarity	NPC284078
0.7325	Intermediate Similarity	NPC107938
0.7325	Intermediate Similarity	NPC294516
0.7312	Intermediate Similarity	NPC279871
0.7312	Intermediate Similarity	NPC159767
0.7312	Intermediate Similarity	NPC26108
0.7312	Intermediate Similarity	NPC471165
0.7312	Intermediate Similarity	NPC17698
0.7312	Intermediate Similarity	NPC165285
0.7312	Intermediate Similarity	NPC155506
0.7305	Intermediate Similarity	NPC475735
0.7302	Intermediate Similarity	NPC211551
0.7295	Intermediate Similarity	NPC324569
0.7293	Intermediate Similarity	NPC169328
0.7289	Intermediate Similarity	NPC94862
0.7287	Intermediate Similarity	NPC21162
0.7287	Intermediate Similarity	NPC321252
0.7287	Intermediate Similarity	NPC252544
0.7284	Intermediate Similarity	NPC97526
0.7284	Intermediate Similarity	NPC119652
0.728	Intermediate Similarity	NPC68055
0.7279	Intermediate Similarity	NPC160493
0.7273	Intermediate Similarity	NPC51345
0.7273	Intermediate Similarity	NPC244336
0.7273	Intermediate Similarity	NPC473360
0.7273	Intermediate Similarity	NPC10286
0.7273	Intermediate Similarity	NPC213
0.7267	Intermediate Similarity	NPC50016
0.7266	Intermediate Similarity	NPC305717
0.726	Intermediate Similarity	NPC33011
0.7259	Intermediate Similarity	NPC80150
0.7248	Intermediate Similarity	NPC9373
0.7246	Intermediate Similarity	NPC62101
0.7246	Intermediate Similarity	NPC95733
0.7241	Intermediate Similarity	NPC238412

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 NPC325651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	115
0.1-0.2	464
0.2-0.3	881
0.3-0.4	1745
0.4-0.5	2787
0.5-0.6	2302
0.6-0.7	736
0.7-0.8	97
0.8-0.85	18
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9134	High Similarity	NPD3136	Phase 2
0.8939	High Similarity	NPD6867	Clinical (unspecified phase)
0.8939	High Similarity	NPD6866	Clinical (unspecified phase)
0.8926	High Similarity	NPD9568	Approved
0.8872	High Similarity	NPD7450	Phase 2
0.8462	Intermediate Similarity	NPD7451	Discontinued
0.8429	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD7978	Discontinued
0.8387	Intermediate Similarity	NPD255	Approved
0.8387	Intermediate Similarity	NPD256	Approved
0.8345	Intermediate Similarity	NPD8019	Approved
0.8345	Intermediate Similarity	NPD7495	Discontinued
0.8284	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD9569	Approved
0.8252	Intermediate Similarity	NPD7523	Phase 3
0.8189	Intermediate Similarity	NPD1759	Phase 1
0.811	Intermediate Similarity	NPD1758	Phase 1
0.8085	Intermediate Similarity	NPD3400	Discontinued
0.8058	Intermediate Similarity	NPD1519	Approved
0.8058	Intermediate Similarity	NPD1537	Approved
0.8058	Intermediate Similarity	NPD1538	Phase 1
0.803	Intermediate Similarity	NPD196	Phase 1
0.8015	Intermediate Similarity	NPD259	Phase 1
0.8	Intermediate Similarity	NPD9537	Phase 1
0.8	Intermediate Similarity	NPD9536	Phase 1
0.7984	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1523	Approved
0.7929	Intermediate Similarity	NPD1522	Approved
0.7914	Intermediate Similarity	NPD1536	Approved
0.7899	Intermediate Similarity	NPD555	Phase 2
0.7794	Intermediate Similarity	NPD2614	Approved
0.7787	Intermediate Similarity	NPD9610	Approved
0.7787	Intermediate Similarity	NPD9608	Approved
0.7786	Intermediate Similarity	NPD1520	Approved
0.7786	Intermediate Similarity	NPD1521	Approved
0.7778	Intermediate Similarity	NPD257	Approved
0.7778	Intermediate Similarity	NPD258	Approved
0.7762	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2561	Approved
0.7744	Intermediate Similarity	NPD2562	Approved
0.7744	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD9718	Approved
0.7724	Intermediate Similarity	NPD7554	Discontinued
0.7698	Intermediate Similarity	NPD6346	Approved
0.7687	Intermediate Similarity	NPD7303	Discontinued
0.7676	Intermediate Similarity	NPD9570	Approved
0.7674	Intermediate Similarity	NPD1348	Approved
0.7651	Intermediate Similarity	NPD3455	Phase 2
0.7622	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD1040	Phase 2
0.7571	Intermediate Similarity	NPD825	Approved
0.7571	Intermediate Similarity	NPD826	Approved
0.7568	Intermediate Similarity	NPD6390	Discontinued
0.7559	Intermediate Similarity	NPD3642	Approved
0.7559	Intermediate Similarity	NPD3643	Approved
0.7559	Intermediate Similarity	NPD3644	Approved
0.7535	Intermediate Similarity	NPD3552	Approved
0.7535	Intermediate Similarity	NPD3554	Approved
0.7535	Intermediate Similarity	NPD3555	Approved
0.7535	Intermediate Similarity	NPD3553	Approved
0.7518	Intermediate Similarity	NPD275	Approved
0.7518	Intermediate Similarity	NPD274	Approved
0.75	Intermediate Similarity	NPD2218	Phase 2
0.75	Intermediate Similarity	NPD2217	Approved
0.7484	Intermediate Similarity	NPD8303	Discontinued
0.748	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD7828	Discontinued
0.7452	Intermediate Similarity	NPD7608	Discontinued
0.7445	Intermediate Similarity	NPD3053	Approved
0.7445	Intermediate Similarity	NPD3055	Approved
0.7438	Intermediate Similarity	NPD9566	Approved
0.7434	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD318	Approved
0.7424	Intermediate Similarity	NPD317	Approved
0.74	Intermediate Similarity	NPD7131	Phase 3
0.7372	Intermediate Similarity	NPD5311	Approved
0.7372	Intermediate Similarity	NPD5310	Approved
0.7353	Intermediate Similarity	NPD6624	Discontinued
0.7333	Intermediate Similarity	NPD3421	Phase 3
0.7319	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2098	Approved
0.7293	Intermediate Similarity	NPD16	Approved
0.7293	Intermediate Similarity	NPD856	Approved
0.7273	Intermediate Similarity	NPD5356	Approved
0.7273	Intermediate Similarity	NPD5355	Approved
0.7267	Intermediate Similarity	NPD3536	Discontinued
0.7252	Intermediate Similarity	NPD2228	Approved
0.7252	Intermediate Similarity	NPD2229	Approved
0.7252	Intermediate Similarity	NPD2234	Approved
0.7241	Intermediate Similarity	NPD6864	Phase 2
0.7241	Intermediate Similarity	NPD6865	Phase 2
0.7239	Intermediate Similarity	NPD5445	Approved
0.7233	Intermediate Similarity	NPD4652	Approved
0.7222	Intermediate Similarity	NPD2568	Approved
0.7219	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD9618	Approved
0.7197	Intermediate Similarity	NPD9614	Approved
0.7192	Intermediate Similarity	NPD2239	Approved
0.7192	Intermediate Similarity	NPD2240	Approved
0.7179	Intermediate Similarity	NPD2097	Approved
0.7176	Intermediate Similarity	NPD9377	Approved
0.7176	Intermediate Similarity	NPD9379	Approved
0.7174	Intermediate Similarity	NPD4659	Approved
0.7172	Intermediate Similarity	NPD6852	Discontinued
0.717	Intermediate Similarity	NPD2888	Approved
0.717	Intermediate Similarity	NPD2017	Approved
0.717	Intermediate Similarity	NPD2889	Approved
0.717	Intermediate Similarity	NPD2890	Approved
0.7143	Intermediate Similarity	NPD6502	Phase 2
0.7133	Intermediate Similarity	NPD6405	Approved
0.7133	Intermediate Similarity	NPD6407	Approved
0.7131	Intermediate Similarity	NPD2933	Approved
0.7131	Intermediate Similarity	NPD2934	Approved
0.7115	Intermediate Similarity	NPD7972	Discontinued
0.7113	Intermediate Similarity	NPD5163	Phase 2
0.7113	Intermediate Similarity	NPD2372	Approved
0.7111	Intermediate Similarity	NPD5304	Approved
0.7111	Intermediate Similarity	NPD5303	Approved
0.7103	Intermediate Similarity	NPD3052	Approved
0.7103	Intermediate Similarity	NPD5314	Approved
0.7103	Intermediate Similarity	NPD3054	Approved
0.7103	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3061	Approved
0.7083	Intermediate Similarity	NPD3062	Approved
0.7083	Intermediate Similarity	NPD3059	Approved
0.708	Intermediate Similarity	NPD3847	Discontinued
0.7073	Intermediate Similarity	NPD2860	Approved
0.7073	Intermediate Similarity	NPD2859	Approved
0.7071	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4103	Phase 2
0.7066	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5981	Approved
0.7055	Intermediate Similarity	NPD3909	Discontinued
0.7047	Intermediate Similarity	NPD2459	Approved
0.7047	Intermediate Similarity	NPD2460	Phase 3
0.7047	Intermediate Similarity	NPD2458	Approved
0.7039	Intermediate Similarity	NPD5556	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2194	Approved
0.7021	Intermediate Similarity	NPD2195	Approved
0.7014	Intermediate Similarity	NPD5745	Approved
0.7	Intermediate Similarity	NPD6746	Phase 2
0.6975	Remote Similarity	NPD5137	Approved
0.697	Remote Similarity	NPD5557	Phase 1
0.6967	Remote Similarity	NPD1812	Approved
0.6967	Remote Similarity	NPD1814	Approved
0.6963	Remote Similarity	NPD5162	Approved
0.6957	Remote Similarity	NPD7485	Phase 3
0.6957	Remote Similarity	NPD3881	Discontinued
0.6957	Remote Similarity	NPD7484	Phase 3
0.6954	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1129	Approved
0.695	Remote Similarity	NPD1135	Approved
0.695	Remote Similarity	NPD1131	Approved
0.695	Remote Similarity	NPD1133	Approved
0.695	Remote Similarity	NPD1134	Approved
0.6944	Remote Similarity	NPD1330	Phase 2
0.6944	Remote Similarity	NPD5299	Approved
0.6944	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4093	Discontinued
0.6929	Remote Similarity	NPD9622	Approved
0.6929	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1755	Approved
0.6928	Remote Similarity	NPD2874	Phase 2
0.6923	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD9615	Approved
0.6912	Remote Similarity	NPD9613	Approved
0.6912	Remote Similarity	NPD9616	Approved
0.6906	Remote Similarity	NPD1535	Discovery
0.6905	Remote Similarity	NPD3020	Approved
0.6905	Remote Similarity	NPD9712	Approved
0.6901	Remote Similarity	NPD7617	Discontinued
0.6899	Remote Similarity	NPD999	Phase 2
0.6887	Remote Similarity	NPD1968	Approved
0.6887	Remote Similarity	NPD1967	Approved
0.6884	Remote Similarity	NPD9384	Approved
0.6884	Remote Similarity	NPD9381	Approved
0.6884	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3125	Approved
0.6879	Remote Similarity	NPD3098	Discontinued
0.6875	Remote Similarity	NPD5746	Approved
0.6875	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4738	Phase 2
0.6875	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6093	Discontinued
0.6861	Remote Similarity	NPD316	Approved
0.6861	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1481	Phase 2
0.6857	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5323	Approved
0.6846	Remote Similarity	NPD6897	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