NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	197.07
Volume:	191.276
LogP:	1.137
LogD:	1.676
LogS:	-2.191
# Rotatable Bonds:	3
TPSA:	81.78
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	2.113
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.592
MDCK Permeability:	6.441070581786335e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.299
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.954
Plasma Protein Binding (PPB):	61.22502517700195%
Volume Distribution (VD):	0.821
Pgp-substrate:	38.62813949584961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.871
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.161
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.202
CYP2C9-substrate:	0.735
CYP2D6-inhibitor:	0.136
CYP2D6-substrate:	0.723
CYP3A4-inhibitor:	0.081
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	9.549
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.698
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.305
Carcinogencity:	0.039
Eye Corrosion:	0.021
Eye Irritation:	0.941
Respiratory Toxicity:	0.185

Download Data

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

Natural Product: NPC98416

Natural Product ID:	NPC98416
*Common Name:**	Methyl 2-Amino-3-Hydroxy-4-Methoxybenzoate
IUPAC Name:	methyl 2-amino-3-hydroxy-4-methoxybenzoate
Synonyms:
Standard InCHIKey:	QBGAIEVOBDWSRU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H11NO4/c1-13-6-4-3-5(9(12)14-2)7(10)8(6)11/h3-4,11H,10H2,1-2H3
SMILES:	COC(=O)c1ccc(c(c1N)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL555451
PubChem CID:	45273209
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002344] Methoxybenzoic acids and derivatives [CHEMONTID:0002346] P-methoxybenzoic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32521	micrococcus sp.	Species	Micrococcaceae	Bacteria	n.a.	Indonesian	n.a.	PMID[19388705]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	11.0	mm	PMID[448915]

☑ 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 NPC98416 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	349
0.1-0.2	2434
0.2-0.3	8429
0.3-0.4	9459
0.4-0.5	5386
0.5-0.6	13036
0.6-0.7	3526
0.7-0.8	77
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7888	Intermediate Similarity	NPC43218
0.7865	Intermediate Similarity	NPC9475
0.7857	Intermediate Similarity	NPC2905
0.7806	Intermediate Similarity	NPC114468
0.7766	Intermediate Similarity	NPC148391
0.7764	Intermediate Similarity	NPC283823
0.7764	Intermediate Similarity	NPC159418
0.776	Intermediate Similarity	NPC163829
0.7739	Intermediate Similarity	NPC134702
0.7739	Intermediate Similarity	NPC182853
0.772	Intermediate Similarity	NPC158551
0.7711	Intermediate Similarity	NPC76478
0.7702	Intermediate Similarity	NPC111888
0.7692	Intermediate Similarity	NPC477825
0.7624	Intermediate Similarity	NPC7560
0.7578	Intermediate Similarity	NPC285776
0.7576	Intermediate Similarity	NPC477826
0.7576	Intermediate Similarity	NPC477827
0.7537	Intermediate Similarity	NPC118189
0.7525	Intermediate Similarity	NPC220241
0.7525	Intermediate Similarity	NPC295479
0.7514	Intermediate Similarity	NPC8467
0.7512	Intermediate Similarity	NPC477828
0.7485	Intermediate Similarity	NPC241392
0.7475	Intermediate Similarity	NPC474366
0.747	Intermediate Similarity	NPC95679
0.747	Intermediate Similarity	NPC125417
0.747	Intermediate Similarity	NPC112068
0.747	Intermediate Similarity	NPC25305
0.747	Intermediate Similarity	NPC110899
0.744	Intermediate Similarity	NPC326065
0.7411	Intermediate Similarity	NPC212123
0.7391	Intermediate Similarity	NPC158654
0.7391	Intermediate Similarity	NPC285254
0.7381	Intermediate Similarity	NPC66518
0.7356	Intermediate Similarity	NPC13249
0.735	Intermediate Similarity	NPC218303
0.7333	Intermediate Similarity	NPC35345
0.7329	Intermediate Similarity	NPC154275
0.731	Intermediate Similarity	NPC469615
0.7301	Intermediate Similarity	NPC226855
0.7289	Intermediate Similarity	NPC155098
0.7284	Intermediate Similarity	NPC281020
0.7267	Intermediate Similarity	NPC113397
0.7267	Intermediate Similarity	NPC469683
0.7267	Intermediate Similarity	NPC315829
0.7262	Intermediate Similarity	NPC314252
0.7246	Intermediate Similarity	NPC139519
0.7241	Intermediate Similarity	NPC176113
0.7228	Intermediate Similarity	NPC91234
0.7228	Intermediate Similarity	NPC470482
0.7228	Intermediate Similarity	NPC470481
0.7192	Intermediate Similarity	NPC268223
0.7186	Intermediate Similarity	NPC45404
0.7178	Intermediate Similarity	NPC32163
0.7178	Intermediate Similarity	NPC16651
0.7151	Intermediate Similarity	NPC287152
0.7143	Intermediate Similarity	NPC472969
0.7143	Intermediate Similarity	NPC208760
0.7143	Intermediate Similarity	NPC305542
0.7136	Intermediate Similarity	NPC87560
0.7136	Intermediate Similarity	NPC195120
0.7135	Intermediate Similarity	NPC908
0.7135	Intermediate Similarity	NPC138438
0.7126	Intermediate Similarity	NPC307006
0.7126	Intermediate Similarity	NPC129889
0.712	Intermediate Similarity	NPC162694
0.7118	Intermediate Similarity	NPC325625
0.7111	Intermediate Similarity	NPC257763
0.711	Intermediate Similarity	NPC473090
0.7108	Intermediate Similarity	NPC30749
0.7108	Intermediate Similarity	NPC264145
0.7102	Intermediate Similarity	NPC476394
0.7102	Intermediate Similarity	NPC98809
0.7091	Intermediate Similarity	NPC94810
0.7079	Intermediate Similarity	NPC121510
0.7079	Intermediate Similarity	NPC171882
0.7079	Intermediate Similarity	NPC85661
0.7073	Intermediate Similarity	NPC117237
0.7073	Intermediate Similarity	NPC203719
0.7067	Intermediate Similarity	NPC118154
0.7067	Intermediate Similarity	NPC157983
0.7066	Intermediate Similarity	NPC50763
0.7048	Intermediate Similarity	NPC299010
0.7045	Intermediate Similarity	NPC469539
0.7045	Intermediate Similarity	NPC469540
0.7041	Intermediate Similarity	NPC274613
0.7035	Intermediate Similarity	NPC50823
0.703	Intermediate Similarity	NPC46679
0.7027	Intermediate Similarity	NPC73280
0.7024	Intermediate Similarity	NPC239855
0.7024	Intermediate Similarity	NPC1321
0.7024	Intermediate Similarity	NPC156124
0.7024	Intermediate Similarity	NPC304929
0.7018	Intermediate Similarity	NPC207516
0.7011	Intermediate Similarity	NPC134975
0.7011	Intermediate Similarity	NPC258307
0.701	Intermediate Similarity	NPC114039
0.701	Intermediate Similarity	NPC206109
0.7005	Intermediate Similarity	NPC315631
0.6995	Remote Similarity	NPC127362
0.6989	Remote Similarity	NPC178097
0.6984	Remote Similarity	NPC472163
0.6983	Remote Similarity	NPC75695
0.6982	Remote Similarity	NPC237330
0.6977	Remote Similarity	NPC4796
0.6954	Remote Similarity	NPC299154
0.6954	Remote Similarity	NPC312256
0.6952	Remote Similarity	NPC128476
0.6952	Remote Similarity	NPC254053
0.6946	Remote Similarity	NPC66905
0.6946	Remote Similarity	NPC298268
0.6941	Remote Similarity	NPC18646
0.694	Remote Similarity	NPC299582
0.6934	Remote Similarity	NPC19175
0.6932	Remote Similarity	NPC287495
0.6932	Remote Similarity	NPC98356
0.6932	Remote Similarity	NPC9370
0.6931	Remote Similarity	NPC283810
0.6927	Remote Similarity	NPC243891
0.6923	Remote Similarity	NPC288743
0.6914	Remote Similarity	NPC177291
0.6914	Remote Similarity	NPC239608
0.6914	Remote Similarity	NPC46161
0.6914	Remote Similarity	NPC50954
0.6914	Remote Similarity	NPC194416
0.691	Remote Similarity	NPC107636
0.6906	Remote Similarity	NPC194095
0.6906	Remote Similarity	NPC327032
0.6906	Remote Similarity	NPC191046
0.6904	Remote Similarity	NPC170333
0.6901	Remote Similarity	NPC475111
0.6901	Remote Similarity	NPC156307
0.6901	Remote Similarity	NPC156892
0.6897	Remote Similarity	NPC110419
0.6893	Remote Similarity	NPC119722
0.6893	Remote Similarity	NPC143903
0.6893	Remote Similarity	NPC165389
0.6893	Remote Similarity	NPC85734
0.6893	Remote Similarity	NPC153644
0.6893	Remote Similarity	NPC226987
0.6893	Remote Similarity	NPC32058
0.6889	Remote Similarity	NPC267091
0.6889	Remote Similarity	NPC124842
0.6888	Remote Similarity	NPC94499
0.6885	Remote Similarity	NPC135006
0.6881	Remote Similarity	NPC38961
0.6878	Remote Similarity	NPC269449
0.6875	Remote Similarity	NPC275278
0.6875	Remote Similarity	NPC240684
0.6875	Remote Similarity	NPC207732
0.6875	Remote Similarity	NPC213900
0.6872	Remote Similarity	NPC473091
0.6872	Remote Similarity	NPC205054
0.6868	Remote Similarity	NPC145425
0.6866	Remote Similarity	NPC172222
0.6851	Remote Similarity	NPC310661
0.6851	Remote Similarity	NPC105827
0.6842	Remote Similarity	NPC5167
0.6842	Remote Similarity	NPC126556
0.6842	Remote Similarity	NPC85613
0.684	Remote Similarity	NPC148124
0.6836	Remote Similarity	NPC262282
0.6833	Remote Similarity	NPC96501
0.6832	Remote Similarity	NPC61779
0.6832	Remote Similarity	NPC156654
0.6831	Remote Similarity	NPC471405
0.6829	Remote Similarity	NPC226794
0.6827	Remote Similarity	NPC290227
0.6821	Remote Similarity	NPC239943
0.6821	Remote Similarity	NPC284409
0.6821	Remote Similarity	NPC112135
0.6818	Remote Similarity	NPC17760
0.6816	Remote Similarity	NPC183655
0.6816	Remote Similarity	NPC287395
0.6814	Remote Similarity	NPC16249
0.6813	Remote Similarity	NPC291510
0.6813	Remote Similarity	NPC469888
0.6813	Remote Similarity	NPC62051
0.6813	Remote Similarity	NPC116850
0.6813	Remote Similarity	NPC238672
0.6813	Remote Similarity	NPC144801
0.6813	Remote Similarity	NPC43872
0.6813	Remote Similarity	NPC197188
0.6812	Remote Similarity	NPC116178
0.6807	Remote Similarity	NPC475236
0.6807	Remote Similarity	NPC321561
0.6806	Remote Similarity	NPC28368
0.6805	Remote Similarity	NPC88667
0.6802	Remote Similarity	NPC326847
0.6796	Remote Similarity	NPC36130
0.6796	Remote Similarity	NPC134905
0.6793	Remote Similarity	NPC296044
0.6793	Remote Similarity	NPC226759
0.6793	Remote Similarity	NPC133984
0.6793	Remote Similarity	NPC472860
0.6793	Remote Similarity	NPC167098
0.6792	Remote Similarity	NPC99724
0.6782	Remote Similarity	NPC105525
0.6782	Remote Similarity	NPC288759

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 NPC98416 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	795
0.2-0.3	1543
0.3-0.4	2240
0.4-0.5	2540
0.5-0.6	1548
0.6-0.7	218
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7931	Intermediate Similarity	NPD2821	Approved
0.7798	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD2899	Discontinued
0.7616	Intermediate Similarity	NPD3684	Discontinued
0.7474	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2672	Discontinued
0.7403	Intermediate Similarity	NPD1220	Phase 1
0.7377	Intermediate Similarity	NPD1221	Approved
0.7159	Intermediate Similarity	NPD824	Approved
0.7094	Intermediate Similarity	NPD683	Approved
0.7073	Intermediate Similarity	NPD9494	Approved
0.7062	Intermediate Similarity	NPD3455	Phase 2
0.7049	Intermediate Similarity	NPD2680	Approved
0.7049	Intermediate Similarity	NPD2681	Approved
0.7049	Intermediate Similarity	NPD2247	Approved
0.7049	Intermediate Similarity	NPD2249	Approved
0.7045	Intermediate Similarity	NPD711	Discontinued
0.7024	Intermediate Similarity	NPD230	Phase 1
0.6983	Remote Similarity	NPD6386	Approved
0.6983	Remote Similarity	NPD6385	Approved
0.6978	Remote Similarity	NPD955	Approved
0.6973	Remote Similarity	NPD5242	Approved
0.6944	Remote Similarity	NPD6625	Approved
0.684	Remote Similarity	NPD4049	Phase 2
0.6823	Remote Similarity	NPD7546	Discontinued
0.6814	Remote Similarity	NPD6296	Discontinued
0.6807	Remote Similarity	NPD257	Approved
0.6807	Remote Similarity	NPD258	Approved
0.6806	Remote Similarity	NPD7038	Approved
0.6806	Remote Similarity	NPD7039	Approved
0.6805	Remote Similarity	NPD259	Phase 1
0.6769	Remote Similarity	NPD1898	Discontinued
0.6765	Remote Similarity	NPD825	Approved
0.6765	Remote Similarity	NPD826	Approved
0.6735	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD555	Phase 2
0.6686	Remote Similarity	NPD75	Approved
0.6686	Remote Similarity	NPD9277	Approved
0.6667	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9569	Approved
0.6667	Remote Similarity	NPD9570	Approved
0.6634	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3298	Approved
0.6632	Remote Similarity	NPD6104	Discontinued
0.6629	Remote Similarity	NPD9278	Suspended
0.6629	Remote Similarity	NPD9276	Approved
0.6629	Remote Similarity	NPD9274	Approved
0.6629	Remote Similarity	NPD9275	Approved
0.6628	Remote Similarity	NPD447	Suspended
0.6618	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4082	Approved
0.6595	Remote Similarity	NPD5353	Approved
0.6579	Remote Similarity	NPD2246	Approved
0.6579	Remote Similarity	NPD2248	Approved
0.657	Remote Similarity	NPD4596	Phase 1
0.6566	Remote Similarity	NPD9269	Phase 2
0.6564	Remote Similarity	NPD9545	Approved
0.6559	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8067	Phase 3
0.6543	Remote Similarity	NPD1559	Discontinued
0.6541	Remote Similarity	NPD1465	Phase 2
0.6541	Remote Similarity	NPD2801	Approved
0.6538	Remote Similarity	NPD3686	Approved
0.6538	Remote Similarity	NPD3687	Approved
0.6538	Remote Similarity	NPD4022	Approved
0.6538	Remote Similarity	NPD3472	Approved
0.6532	Remote Similarity	NPD275	Approved
0.6532	Remote Similarity	NPD274	Approved
0.6524	Remote Similarity	NPD4493	Discontinued
0.6524	Remote Similarity	NPD1945	Phase 1
0.652	Remote Similarity	NPD2339	Phase 3
0.6513	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD5071	Phase 2
0.65	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD9536	Phase 1
0.6491	Remote Similarity	NPD9537	Phase 1
0.6486	Remote Similarity	NPD1934	Approved
0.6486	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1670	Discontinued
0.6476	Remote Similarity	NPD3893	Discontinued
0.6476	Remote Similarity	NPD5860	Discontinued
0.6476	Remote Similarity	NPD3372	Discontinued
0.6474	Remote Similarity	NPD1293	Approved
0.6474	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3297	Approved
0.6471	Remote Similarity	NPD3882	Suspended
0.6465	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7559	Phase 2
0.6429	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4628	Phase 3
0.6422	Remote Similarity	NPD4668	Phase 2
0.6416	Remote Similarity	NPD2674	Phase 3
0.6415	Remote Similarity	NPD3888	Discontinued
0.6415	Remote Similarity	NPD4494	Approved
0.6415	Remote Similarity	NPD4492	Approved
0.6413	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7922	Phase 1
0.6409	Remote Similarity	NPD1511	Approved
0.6406	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3965	Phase 1
0.6389	Remote Similarity	NPD6190	Approved
0.6387	Remote Similarity	NPD6232	Discontinued
0.6385	Remote Similarity	NPD4455	Discontinued
0.6382	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD2906	Approved
0.6381	Remote Similarity	NPD2907	Approved
0.6378	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7685	Pre-registration
0.6373	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD3144	Approved
0.6358	Remote Similarity	NPD3145	Approved
0.6355	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD552	Approved
0.6353	Remote Similarity	NPD553	Approved
0.6353	Remote Similarity	NPD9567	Approved
0.6345	Remote Similarity	NPD1891	Discontinued
0.6344	Remote Similarity	NPD2366	Approved
0.634	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD1512	Approved
0.633	Remote Similarity	NPD3817	Phase 2
0.633	Remote Similarity	NPD5977	Approved
0.633	Remote Similarity	NPD5978	Approved
0.6325	Remote Similarity	NPD9268	Approved
0.6313	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD5496	Approved
0.6304	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7585	Approved
0.6303	Remote Similarity	NPD2514	Approved
0.6302	Remote Similarity	NPD5186	Approved
0.6302	Remote Similarity	NPD5183	Approved
0.6296	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD196	Phase 1
0.6293	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7473	Discontinued
0.6284	Remote Similarity	NPD3146	Approved
0.6284	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD2978	Approved
0.6277	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD2977	Approved
0.6271	Remote Similarity	NPD9279	Approved
0.6261	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD2836	Approved
0.6257	Remote Similarity	NPD6873	Phase 2
0.6257	Remote Similarity	NPD3778	Approved
0.6256	Remote Similarity	NPD3818	Discontinued
0.6256	Remote Similarity	NPD7583	Approved
0.6256	Remote Similarity	NPD2163	Approved
0.6256	Remote Similarity	NPD7263	Phase 2
0.6244	Remote Similarity	NPD6297	Approved
0.6244	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD2845	Phase 2
0.6238	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD2843	Phase 2
0.6235	Remote Similarity	NPD9622	Approved
0.6235	Remote Similarity	NPD228	Approved
0.6232	Remote Similarity	NPD6874	Approved
0.6231	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.623	Remote Similarity	NPD4357	Discontinued
0.6225	Remote Similarity	NPD7125	Discontinued
0.6217	Remote Similarity	NPD1483	Discontinued
0.6215	Remote Similarity	NPD4206	Approved
0.621	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD5617	Suspended
0.6201	Remote Similarity	NPD2935	Discontinued
0.6199	Remote Similarity	NPD1574	Approved
0.6196	Remote Similarity	NPD4123	Phase 3
0.6193	Remote Similarity	NPD2325	Approved
0.619	Remote Similarity	NPD9272	Approved
0.6188	Remote Similarity	NPD3060	Approved
0.6188	Remote Similarity	NPD2792	Approved
0.6186	Remote Similarity	NPD4083	Discontinued
0.6186	Remote Similarity	NPD2215	Approved
0.6186	Remote Similarity	NPD2216	Approved
0.6184	Remote Similarity	NPD4420	Approved
0.6181	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD2434	Approved
0.6178	Remote Similarity	NPD6962	Phase 2
0.6175	Remote Similarity	NPD5025	Approved
0.6171	Remote Similarity	NPD4505	Phase 1
0.6169	Remote Similarity	NPD3154	Approved
0.6169	Remote Similarity	NPD3153	Approved
0.6168	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5914	Approved
0.6165	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD2186	Approved
0.6162	Remote Similarity	NPD3823	Discontinued
0.6162	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4467	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