NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	164.05
Volume:	168.852
LogP:	1.799
LogD:	1.642
LogS:	-3.148
# Rotatable Bonds:	3
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	1.589
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.493
MDCK Permeability:	2.1002055291319266e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.733

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	84.17603302001953%
Volume Distribution (VD):	0.91
Pgp-substrate:	9.009693145751953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.253
CYP2C19-inhibitor:	0.361
CYP2C19-substrate:	0.114
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.564
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.283
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	7.576
Half-life (T1/2):	0.828

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.323
Carcinogencity:	0.023
Eye Corrosion:	0.418
Eye Irritation:	0.993
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC188895

Natural Product ID:	NPC188895
*Common Name:**	Methyl 4-Formylbenzoate
IUPAC Name:	methyl 4-formylbenzoate
Synonyms:
Standard InCHIKey:	FEIOASZZURHTHB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8O3/c1-12-9(11)8-4-2-7(6-10)3-5-8/h2-6H,1H3
SMILES:	COC(=O)c1ccc(cc1)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1607943
PubChem CID:	15294
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Potency	16

Activity Type	# Activity
Individual Protein	7
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[561404]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	398.1	nM	PMID[561404]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	1.4	nM	PMID[561404]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[561404]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	891.3	nM	PMID[561404]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[561403]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	8912.5	nM	PMID[561403]
NPT2	Others	Unspecified		Potency	n.a.	68659.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27559.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61192.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24361.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2733.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	64816.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	57767.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	28952.5	nM	PubChem BioAssay data set

☑ 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 NPC188895 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	280
0.1-0.2	1878
0.2-0.3	4396
0.3-0.4	11102
0.4-0.5	10712
0.5-0.6	10974
0.6-0.7	2966
0.7-0.8	314
0.8-0.85	49
0.85-0.9	14
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC70624
0.9579	High Similarity	NPC203925
0.9368	High Similarity	NPC249912
0.9368	High Similarity	NPC92754
0.9368	High Similarity	NPC276775
0.9362	High Similarity	NPC130398
0.9271	High Similarity	NPC35448
0.9271	High Similarity	NPC78701
0.9271	High Similarity	NPC225060
0.9175	High Similarity	NPC146351
0.898	High Similarity	NPC118343
0.89	High Similarity	NPC301943
0.89	High Similarity	NPC474365
0.8889	High Similarity	NPC42211
0.8788	High Similarity	NPC325497
0.8776	High Similarity	NPC253423
0.8641	High Similarity	NPC119271
0.8632	High Similarity	NPC173443
0.8627	High Similarity	NPC31786
0.86	High Similarity	NPC217621
0.8558	High Similarity	NPC56493
0.8544	High Similarity	NPC269457
0.8529	High Similarity	NPC89886
0.8529	High Similarity	NPC60679
0.8511	High Similarity	NPC318107
0.8505	High Similarity	NPC128368
0.8491	Intermediate Similarity	NPC167504
0.8485	Intermediate Similarity	NPC61944
0.8476	Intermediate Similarity	NPC10251
0.8476	Intermediate Similarity	NPC83628
0.8476	Intermediate Similarity	NPC469636
0.8476	Intermediate Similarity	NPC17417
0.8476	Intermediate Similarity	NPC474364
0.8476	Intermediate Similarity	NPC265407
0.8431	Intermediate Similarity	NPC304873
0.8431	Intermediate Similarity	NPC25458
0.8421	Intermediate Similarity	NPC89377
0.8396	Intermediate Similarity	NPC174099
0.8396	Intermediate Similarity	NPC214067
0.8396	Intermediate Similarity	NPC196246
0.8396	Intermediate Similarity	NPC93084
0.8396	Intermediate Similarity	NPC251854
0.8365	Intermediate Similarity	NPC209632
0.8333	Intermediate Similarity	NPC473325
0.8318	Intermediate Similarity	NPC474157
0.8318	Intermediate Similarity	NPC210089
0.8318	Intermediate Similarity	NPC1082
0.8318	Intermediate Similarity	NPC476003
0.8318	Intermediate Similarity	NPC260818
0.8318	Intermediate Similarity	NPC305912
0.8302	Intermediate Similarity	NPC85493
0.8286	Intermediate Similarity	NPC37622
0.8286	Intermediate Similarity	NPC30594
0.8283	Intermediate Similarity	NPC261181
0.8269	Intermediate Similarity	NPC114594
0.8257	Intermediate Similarity	NPC307651
0.8252	Intermediate Similarity	NPC45613
0.8247	Intermediate Similarity	NPC220893
0.8241	Intermediate Similarity	NPC321852
0.8241	Intermediate Similarity	NPC82899
0.8241	Intermediate Similarity	NPC270699
0.8211	Intermediate Similarity	NPC58616
0.819	Intermediate Similarity	NPC105899
0.8165	Intermediate Similarity	NPC161611
0.8165	Intermediate Similarity	NPC272524
0.8163	Intermediate Similarity	NPC62765
0.8137	Intermediate Similarity	NPC229242
0.8131	Intermediate Similarity	NPC269023
0.8131	Intermediate Similarity	NPC99846
0.8108	Intermediate Similarity	NPC149691
0.8091	Intermediate Similarity	NPC308744
0.8091	Intermediate Similarity	NPC153053
0.8091	Intermediate Similarity	NPC474363
0.8085	Intermediate Similarity	NPC106313
0.8081	Intermediate Similarity	NPC119631
0.8073	Intermediate Similarity	NPC474314
0.8073	Intermediate Similarity	NPC158282
0.8073	Intermediate Similarity	NPC79496
0.8073	Intermediate Similarity	NPC54626
0.8039	Intermediate Similarity	NPC270654
0.8037	Intermediate Similarity	NPC249811
0.8021	Intermediate Similarity	NPC294134
0.8018	Intermediate Similarity	NPC210092
0.8018	Intermediate Similarity	NPC474685
0.8018	Intermediate Similarity	NPC81808
0.8	Intermediate Similarity	NPC474176
0.8	Intermediate Similarity	NPC288903
0.7979	Intermediate Similarity	NPC100039
0.7959	Intermediate Similarity	NPC304760
0.7928	Intermediate Similarity	NPC53953
0.7909	Intermediate Similarity	NPC57879
0.7863	Intermediate Similarity	NPC472703
0.7857	Intermediate Similarity	NPC474095
0.7857	Intermediate Similarity	NPC306740
0.7838	Intermediate Similarity	NPC13784
0.783	Intermediate Similarity	NPC255676
0.7812	Intermediate Similarity	NPC197581
0.7807	Intermediate Similarity	NPC45104
0.7807	Intermediate Similarity	NPC240664
0.7807	Intermediate Similarity	NPC228318
0.7807	Intermediate Similarity	NPC217423
0.7798	Intermediate Similarity	NPC318327
0.7797	Intermediate Similarity	NPC472704
0.7788	Intermediate Similarity	NPC135730
0.7788	Intermediate Similarity	NPC188907
0.7788	Intermediate Similarity	NPC220540
0.7788	Intermediate Similarity	NPC100353
0.7768	Intermediate Similarity	NPC196075
0.7768	Intermediate Similarity	NPC237366
0.7768	Intermediate Similarity	NPC477411
0.7759	Intermediate Similarity	NPC473243
0.7748	Intermediate Similarity	NPC66208
0.7739	Intermediate Similarity	NPC94298
0.7739	Intermediate Similarity	NPC27633
0.7739	Intermediate Similarity	NPC94637
0.7736	Intermediate Similarity	NPC284477
0.7719	Intermediate Similarity	NPC128825
0.7719	Intermediate Similarity	NPC131192
0.7714	Intermediate Similarity	NPC228435
0.7699	Intermediate Similarity	NPC228936
0.7699	Intermediate Similarity	NPC252004
0.7692	Intermediate Similarity	NPC50872
0.7672	Intermediate Similarity	NPC137710
0.7672	Intermediate Similarity	NPC90522
0.7672	Intermediate Similarity	NPC328459
0.7664	Intermediate Similarity	NPC234305
0.7658	Intermediate Similarity	NPC243355
0.7653	Intermediate Similarity	NPC252067
0.7652	Intermediate Similarity	NPC469574
0.7642	Intermediate Similarity	NPC282895
0.7632	Intermediate Similarity	NPC226093
0.7624	Intermediate Similarity	NPC240108
0.7624	Intermediate Similarity	NPC213156
0.7615	Intermediate Similarity	NPC1065
0.7607	Intermediate Similarity	NPC72977
0.7603	Intermediate Similarity	NPC472706
0.7593	Intermediate Similarity	NPC85977
0.7589	Intermediate Similarity	NPC23332
0.7589	Intermediate Similarity	NPC212415
0.7586	Intermediate Similarity	NPC171023
0.7579	Intermediate Similarity	NPC167577
0.7579	Intermediate Similarity	NPC78517
0.7565	Intermediate Similarity	NPC316062
0.7553	Intermediate Similarity	NPC287790
0.7553	Intermediate Similarity	NPC3672
0.7549	Intermediate Similarity	NPC110704
0.7547	Intermediate Similarity	NPC98911
0.7547	Intermediate Similarity	NPC472318
0.7545	Intermediate Similarity	NPC470391
0.7544	Intermediate Similarity	NPC186933
0.7542	Intermediate Similarity	NPC144547
0.7541	Intermediate Similarity	NPC472707
0.7526	Intermediate Similarity	NPC323103
0.7525	Intermediate Similarity	NPC9822
0.7521	Intermediate Similarity	NPC61779
0.7521	Intermediate Similarity	NPC472708
0.7521	Intermediate Similarity	NPC470765
0.75	Intermediate Similarity	NPC121800
0.75	Intermediate Similarity	NPC228739
0.75	Intermediate Similarity	NPC160382
0.75	Intermediate Similarity	NPC183648
0.7479	Intermediate Similarity	NPC26285
0.7476	Intermediate Similarity	NPC77273
0.7474	Intermediate Similarity	NPC176228
0.7459	Intermediate Similarity	NPC473220
0.7459	Intermediate Similarity	NPC470753
0.7458	Intermediate Similarity	NPC230951
0.7458	Intermediate Similarity	NPC988
0.7458	Intermediate Similarity	NPC289432
0.7458	Intermediate Similarity	NPC233282
0.7453	Intermediate Similarity	NPC210529
0.7453	Intermediate Similarity	NPC160548
0.7453	Intermediate Similarity	NPC175852
0.7451	Intermediate Similarity	NPC86670
0.7451	Intermediate Similarity	NPC70940
0.7451	Intermediate Similarity	NPC185501
0.7451	Intermediate Similarity	NPC274455
0.7449	Intermediate Similarity	NPC39600
0.7449	Intermediate Similarity	NPC285773
0.7449	Intermediate Similarity	NPC270507
0.7447	Intermediate Similarity	NPC78500
0.7438	Intermediate Similarity	NPC246166
0.7438	Intermediate Similarity	NPC125053
0.7438	Intermediate Similarity	NPC295664
0.7431	Intermediate Similarity	NPC249067
0.7426	Intermediate Similarity	NPC153308
0.7426	Intermediate Similarity	NPC329064
0.7423	Intermediate Similarity	NPC89950
0.7423	Intermediate Similarity	NPC303245
0.7423	Intermediate Similarity	NPC73978
0.7417	Intermediate Similarity	NPC223351
0.7417	Intermediate Similarity	NPC69403
0.7417	Intermediate Similarity	NPC291189
0.7414	Intermediate Similarity	NPC470860
0.7411	Intermediate Similarity	NPC234639
0.7407	Intermediate Similarity	NPC84325
0.7396	Intermediate Similarity	NPC170484
0.7395	Intermediate Similarity	NPC295317
0.7391	Intermediate Similarity	NPC221275
0.7391	Intermediate Similarity	NPC476357

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 NPC188895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	998
0.2-0.3	1388
0.3-0.4	3045
0.4-0.5	2188
0.5-0.6	963
0.6-0.7	230
0.7-0.8	57
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.898	High Similarity	NPD1238	Approved
0.8627	High Similarity	NPD164	Approved
0.8511	High Similarity	NPD9259	Approved
0.8511	High Similarity	NPD9257	Approved
0.8476	Intermediate Similarity	NPD2182	Approved
0.8318	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8283	Intermediate Similarity	NPD1202	Approved
0.8163	Intermediate Similarity	NPD9256	Approved
0.8163	Intermediate Similarity	NPD9258	Approved
0.7843	Intermediate Similarity	NPD9260	Approved
0.7778	Intermediate Similarity	NPD6287	Discontinued
0.7739	Intermediate Similarity	NPD9545	Approved
0.7719	Intermediate Similarity	NPD9493	Approved
0.7677	Intermediate Similarity	NPD1087	Approved
0.7596	Intermediate Similarity	NPD1989	Approved
0.7589	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD9508	Approved
0.7579	Intermediate Similarity	NPD9490	Approved
0.7544	Intermediate Similarity	NPD5951	Approved
0.7525	Intermediate Similarity	NPD800	Approved
0.7477	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD225	Approved
0.7474	Intermediate Similarity	NPD227	Approved
0.7453	Intermediate Similarity	NPD9495	Approved
0.7451	Intermediate Similarity	NPD1086	Approved
0.7451	Intermediate Similarity	NPD1089	Approved
0.7451	Intermediate Similarity	NPD1090	Approved
0.7449	Intermediate Similarity	NPD9491	Approved
0.7431	Intermediate Similarity	NPD1237	Approved
0.7419	Intermediate Similarity	NPD7008	Discontinued
0.7419	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2066	Phase 3
0.7339	Intermediate Similarity	NPD1929	Approved
0.7339	Intermediate Similarity	NPD1930	Approved
0.7339	Intermediate Similarity	NPD9261	Approved
0.7339	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1088	Approved
0.7304	Intermediate Similarity	NPD1241	Discontinued
0.7295	Intermediate Similarity	NPD2199	Approved
0.7295	Intermediate Similarity	NPD2198	Approved
0.7257	Intermediate Similarity	NPD2067	Discontinued
0.7248	Intermediate Similarity	NPD1932	Approved
0.7245	Intermediate Similarity	NPD226	Approved
0.7238	Intermediate Similarity	NPD1563	Approved
0.7236	Intermediate Similarity	NPD553	Approved
0.7236	Intermediate Similarity	NPD552	Approved
0.7236	Intermediate Similarity	NPD9567	Approved
0.7217	Intermediate Similarity	NPD5277	Phase 2
0.7212	Intermediate Similarity	NPD1239	Approved
0.7177	Intermediate Similarity	NPD1019	Discontinued
0.717	Intermediate Similarity	NPD1693	Approved
0.7167	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD1282	Approved
0.7143	Intermediate Similarity	NPD3134	Approved
0.7132	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD9717	Approved
0.7131	Intermediate Similarity	NPD3972	Approved
0.7115	Intermediate Similarity	NPD3673	Approved
0.7115	Intermediate Similarity	NPD3672	Approved
0.7099	Intermediate Similarity	NPD1551	Phase 2
0.708	Intermediate Similarity	NPD9264	Approved
0.708	Intermediate Similarity	NPD9263	Approved
0.708	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1358	Approved
0.708	Intermediate Similarity	NPD9267	Approved
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7049	Intermediate Similarity	NPD1281	Approved
0.7037	Intermediate Similarity	NPD1566	Phase 3
0.7037	Intermediate Similarity	NPD1565	Approved
0.7037	Intermediate Similarity	NPD1564	Approved
0.7018	Intermediate Similarity	NPD2329	Discontinued
0.7018	Intermediate Similarity	NPD9266	Approved
0.7018	Intermediate Similarity	NPD74	Approved
0.6984	Remote Similarity	NPD9494	Approved
0.6977	Remote Similarity	NPD4307	Phase 2
0.6967	Remote Similarity	NPD1889	Phase 1
0.6964	Remote Similarity	NPD5909	Discontinued
0.6957	Remote Similarity	NPD1317	Discontinued
0.6953	Remote Similarity	NPD411	Approved
0.6949	Remote Similarity	NPD2629	Approved
0.6935	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2347	Approved
0.6917	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4198	Discontinued
0.6885	Remote Similarity	NPD1778	Approved
0.688	Remote Similarity	NPD1283	Approved
0.688	Remote Similarity	NPD1876	Approved
0.6875	Remote Similarity	NPD6647	Phase 2
0.6852	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3373	Approved
0.6829	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD650	Approved
0.6825	Remote Similarity	NPD1203	Approved
0.6818	Remote Similarity	NPD5926	Approved
0.6804	Remote Similarity	NPD9716	Approved
0.6803	Remote Similarity	NPD5691	Approved
0.6794	Remote Similarity	NPD230	Phase 1
0.6791	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2798	Approved
0.6769	Remote Similarity	NPD7713	Phase 3
0.6767	Remote Similarity	NPD4308	Phase 3
0.6765	Remote Similarity	NPD4628	Phase 3
0.6759	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD9697	Approved
0.6752	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD17	Approved
0.6748	Remote Similarity	NPD1104	Approved
0.6746	Remote Similarity	NPD1888	Phase 1
0.6733	Remote Similarity	NPD942	Approved
0.6721	Remote Similarity	NPD1894	Discontinued
0.6698	Remote Similarity	NPD5346	Phase 2
0.6698	Remote Similarity	NPD689	Discontinued
0.6698	Remote Similarity	NPD5347	Phase 2
0.6695	Remote Similarity	NPD969	Suspended
0.6692	Remote Similarity	NPD2670	Approved
0.6692	Remote Similarity	NPD2569	Approved
0.6692	Remote Similarity	NPD3764	Approved
0.6692	Remote Similarity	NPD2313	Discontinued
0.6692	Remote Similarity	NPD2567	Approved
0.6667	Remote Similarity	NPD9281	Approved
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD4793	Discontinued
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD9294	Approved
0.6667	Remote Similarity	NPD447	Suspended
0.6642	Remote Similarity	NPD1109	Approved
0.6642	Remote Similarity	NPD3170	Approved
0.6642	Remote Similarity	NPD7003	Approved
0.6642	Remote Similarity	NPD1110	Approved
0.6641	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6039	Approved
0.6615	Remote Similarity	NPD6966	Discovery
0.6614	Remote Similarity	NPD5667	Approved
0.6613	Remote Similarity	NPD4626	Approved
0.6607	Remote Similarity	NPD7798	Approved
0.6593	Remote Similarity	NPD2935	Discontinued
0.6591	Remote Similarity	NPD2979	Phase 3
0.6587	Remote Similarity	NPD1608	Approved
0.6587	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7609	Phase 3
0.6565	Remote Similarity	NPD9471	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7236	Approved
0.6532	Remote Similarity	NPD1245	Approved
0.6529	Remote Similarity	NPD1246	Approved
0.6525	Remote Similarity	NPD1752	Approved
0.6525	Remote Similarity	NPD5236	Approved
0.6525	Remote Similarity	NPD5235	Approved
0.6525	Remote Similarity	NPD5240	Approved
0.6525	Remote Similarity	NPD4234	Approved
0.6525	Remote Similarity	NPD5237	Approved
0.6525	Remote Similarity	NPD5239	Approved
0.6525	Remote Similarity	NPD1756	Approved
0.6525	Remote Similarity	NPD4233	Approved
0.6522	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2799	Discontinued
0.6514	Remote Similarity	NPD7631	Approved
0.6512	Remote Similarity	NPD6085	Phase 2
0.6512	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD506	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6858	Approved
0.65	Remote Similarity	NPD7094	Approved
0.6496	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD1607	Approved
0.648	Remote Similarity	NPD5306	Approved
0.648	Remote Similarity	NPD5305	Approved
0.6471	Remote Similarity	NPD2201	Approved
0.6466	Remote Similarity	NPD3140	Approved
0.6466	Remote Similarity	NPD3142	Approved
0.6457	Remote Similarity	NPD6637	Approved
0.6449	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD3267	Approved
0.6434	Remote Similarity	NPD1164	Approved
0.6434	Remote Similarity	NPD2797	Approved
0.6434	Remote Similarity	NPD7239	Suspended
0.6434	Remote Similarity	NPD3266	Approved
0.6429	Remote Similarity	NPD4136	Approved
0.6429	Remote Similarity	NPD4135	Approved
0.6429	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4106	Approved
0.6429	Remote Similarity	NPD3496	Discontinued
0.6429	Remote Similarity	NPD3495	Discontinued
0.6423	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD9250	Approved
0.6408	Remote Similarity	NPD6273	Approved
0.6406	Remote Similarity	NPD5157	Phase 1
0.6406	Remote Similarity	NPD5159	Phase 2
0.6406	Remote Similarity	NPD4359	Approved
0.6406	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD3748	Approved

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