NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.08
Volume:	261.72
LogP:	1.3
LogD:	1.175
LogS:	-1.727
# Rotatable Bonds:	3
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	2.411
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.268
MDCK Permeability:	4.46954982180614e-06
Pgp-inhibitor:	0.05
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.602
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	81.9097900390625%
Volume Distribution (VD):	0.648
Pgp-substrate:	10.637178421020508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.438
CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.277
CYP2C9-substrate:	0.701
CYP2D6-inhibitor:	0.394
CYP2D6-substrate:	0.603
CYP3A4-inhibitor:	0.146
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	15.347
Half-life (T1/2):	0.962

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.446
AMES Toxicity:	0.683
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.951
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.935
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC472071

Natural Product ID:	NPC472071
*Common Name:**	DEEJTWOVRVKJGM-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DEEJTWOVRVKJGM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O5/c15-7-9-5-10(16)6-13(18)11(9)3-8-1-2-12(17)14(19)4-8/h1-2,4-6,15-19H,3,7H2
SMILES:	C1=CC(=C(C=C1CC2=C(C=C(C=C2O)O)CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3337528
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO33084	Geosmithia langdonii	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25084548]
NPO33084	Geosmithia langdonii	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30298736]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	13000.0	nM	PMID[564723]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	22000.0	nM	PMID[564723]

☑ 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 NPC472071 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	458
0.1-0.2	1670
0.2-0.3	5259
0.3-0.4	13266
0.4-0.5	5284
0.5-0.6	5218
0.6-0.7	8302
0.7-0.8	2695
0.8-0.85	461
0.85-0.9	75
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC471485
0.9224	High Similarity	NPC217174
0.9211	High Similarity	NPC472893
0.9196	High Similarity	NPC268032
0.9153	High Similarity	NPC237667
0.9	High Similarity	NPC53567
0.8992	High Similarity	NPC39029
0.8974	High Similarity	NPC144343
0.8929	High Similarity	NPC114392
0.8929	High Similarity	NPC105727
0.8929	High Similarity	NPC58427
0.8929	High Similarity	NPC34864
0.8889	High Similarity	NPC277588
0.8852	High Similarity	NPC33654
0.885	High Similarity	NPC202647
0.8839	High Similarity	NPC176527
0.8824	High Similarity	NPC223451
0.8793	High Similarity	NPC120280
0.877	High Similarity	NPC224342
0.8761	High Similarity	NPC233835
0.875	High Similarity	NPC24125
0.874	High Similarity	NPC474453
0.8739	High Similarity	NPC191866
0.8729	High Similarity	NPC470760
0.8707	High Similarity	NPC261343
0.8696	High Similarity	NPC257430
0.8696	High Similarity	NPC179002
0.8696	High Similarity	NPC187583
0.8661	High Similarity	NPC292452
0.8651	High Similarity	NPC126836
0.8644	High Similarity	NPC115808
0.864	High Similarity	NPC148366
0.864	High Similarity	NPC311293
0.8632	High Similarity	NPC107240
0.8621	High Similarity	NPC473521
0.8609	High Similarity	NPC475018
0.8609	High Similarity	NPC120982
0.8609	High Similarity	NPC174096
0.8609	High Similarity	NPC79793
0.8609	High Similarity	NPC226401
0.8609	High Similarity	NPC147634
0.8595	High Similarity	NPC470414
0.8584	High Similarity	NPC248904
0.8583	High Similarity	NPC15543
0.8571	High Similarity	NPC212015
0.8571	High Similarity	NPC30506
0.8571	High Similarity	NPC102216
0.8571	High Similarity	NPC12278
0.8571	High Similarity	NPC471511
0.856	High Similarity	NPC266555
0.855	High Similarity	NPC184613
0.8538	High Similarity	NPC234952
0.8537	High Similarity	NPC84086
0.8527	High Similarity	NPC160697
0.8522	High Similarity	NPC62258
0.8522	High Similarity	NPC55617
0.8516	High Similarity	NPC126029
0.8516	High Similarity	NPC15658
0.8516	High Similarity	NPC261619
0.8516	High Similarity	NPC219876
0.8516	High Similarity	NPC61477
0.8516	High Similarity	NPC185604
0.8516	High Similarity	NPC78770
0.8496	Intermediate Similarity	NPC239291
0.8492	Intermediate Similarity	NPC154866
0.8475	Intermediate Similarity	NPC473137
0.8473	Intermediate Similarity	NPC46277
0.8473	Intermediate Similarity	NPC86605
0.8473	Intermediate Similarity	NPC156948
0.8473	Intermediate Similarity	NPC301765
0.8473	Intermediate Similarity	NPC3072
0.8462	Intermediate Similarity	NPC256262
0.8462	Intermediate Similarity	NPC43525
0.845	Intermediate Similarity	NPC32778
0.8438	Intermediate Similarity	NPC268342
0.8438	Intermediate Similarity	NPC220825
0.8438	Intermediate Similarity	NPC232275
0.8438	Intermediate Similarity	NPC474017
0.8438	Intermediate Similarity	NPC268266
0.8438	Intermediate Similarity	NPC42760
0.843	Intermediate Similarity	NPC176893
0.8425	Intermediate Similarity	NPC170844
0.8425	Intermediate Similarity	NPC476968
0.8413	Intermediate Similarity	NPC324112
0.8413	Intermediate Similarity	NPC282000
0.8413	Intermediate Similarity	NPC124452
0.8413	Intermediate Similarity	NPC159968
0.8413	Intermediate Similarity	NPC293054
0.8413	Intermediate Similarity	NPC246620
0.8413	Intermediate Similarity	NPC169474
0.8413	Intermediate Similarity	NPC82679
0.8413	Intermediate Similarity	NPC236791
0.8413	Intermediate Similarity	NPC74817
0.8409	Intermediate Similarity	NPC32630
0.8409	Intermediate Similarity	NPC230124
0.8409	Intermediate Similarity	NPC6300
0.8409	Intermediate Similarity	NPC114171
0.8407	Intermediate Similarity	NPC119860
0.8397	Intermediate Similarity	NPC133025
0.8397	Intermediate Similarity	NPC202846
0.8397	Intermediate Similarity	NPC143139
0.8393	Intermediate Similarity	NPC143659
0.8393	Intermediate Similarity	NPC110764
0.8393	Intermediate Similarity	NPC100340
0.8387	Intermediate Similarity	NPC473451
0.8387	Intermediate Similarity	NPC228922
0.8387	Intermediate Similarity	NPC197757
0.8387	Intermediate Similarity	NPC136319
0.8387	Intermediate Similarity	NPC121115
0.8385	Intermediate Similarity	NPC7515
0.8385	Intermediate Similarity	NPC206737
0.8385	Intermediate Similarity	NPC56764
0.8385	Intermediate Similarity	NPC188378
0.8385	Intermediate Similarity	NPC276026
0.8385	Intermediate Similarity	NPC555
0.8385	Intermediate Similarity	NPC469659
0.8385	Intermediate Similarity	NPC289258
0.8376	Intermediate Similarity	NPC476632
0.8376	Intermediate Similarity	NPC165770
0.8376	Intermediate Similarity	NPC225679
0.8376	Intermediate Similarity	NPC4493
0.8372	Intermediate Similarity	NPC6451
0.8362	Intermediate Similarity	NPC228343
0.8362	Intermediate Similarity	NPC254833
0.8361	Intermediate Similarity	NPC475245
0.8359	Intermediate Similarity	NPC51840
0.8359	Intermediate Similarity	NPC311680
0.8359	Intermediate Similarity	NPC299221
0.8359	Intermediate Similarity	NPC234488
0.8347	Intermediate Similarity	NPC48781
0.8347	Intermediate Similarity	NPC9592
0.8346	Intermediate Similarity	NPC206615
0.8346	Intermediate Similarity	NPC186843
0.8346	Intermediate Similarity	NPC98631
0.8346	Intermediate Similarity	NPC46274
0.8346	Intermediate Similarity	NPC470213
0.8346	Intermediate Similarity	NPC226331
0.8333	Intermediate Similarity	NPC471350
0.8333	Intermediate Similarity	NPC103823
0.8333	Intermediate Similarity	NPC214406
0.8333	Intermediate Similarity	NPC94994
0.8333	Intermediate Similarity	NPC44748
0.8333	Intermediate Similarity	NPC223953
0.8333	Intermediate Similarity	NPC18924
0.8333	Intermediate Similarity	NPC474839
0.8333	Intermediate Similarity	NPC28730
0.8333	Intermediate Similarity	NPC151656
0.8333	Intermediate Similarity	NPC78974
0.8333	Intermediate Similarity	NPC223136
0.8321	Intermediate Similarity	NPC313081
0.8321	Intermediate Similarity	NPC240279
0.8321	Intermediate Similarity	NPC69029
0.8321	Intermediate Similarity	NPC294884
0.8321	Intermediate Similarity	NPC158142
0.8321	Intermediate Similarity	NPC108198
0.8321	Intermediate Similarity	NPC10314
0.8321	Intermediate Similarity	NPC164787
0.8321	Intermediate Similarity	NPC180602
0.8321	Intermediate Similarity	NPC55239
0.8321	Intermediate Similarity	NPC200557
0.8321	Intermediate Similarity	NPC214853
0.832	Intermediate Similarity	NPC206487
0.832	Intermediate Similarity	NPC5796
0.8319	Intermediate Similarity	NPC168393
0.8319	Intermediate Similarity	NPC12656
0.8308	Intermediate Similarity	NPC475840
0.8308	Intermediate Similarity	NPC11060
0.8306	Intermediate Similarity	NPC41562
0.8306	Intermediate Similarity	NPC471794
0.8305	Intermediate Similarity	NPC166995
0.8304	Intermediate Similarity	NPC248573
0.8304	Intermediate Similarity	NPC275053
0.8304	Intermediate Similarity	NPC223393
0.8304	Intermediate Similarity	NPC161571
0.8295	Intermediate Similarity	NPC45715
0.8295	Intermediate Similarity	NPC474356
0.8295	Intermediate Similarity	NPC12275
0.8291	Intermediate Similarity	NPC224870
0.8284	Intermediate Similarity	NPC265075
0.8281	Intermediate Similarity	NPC58164
0.8281	Intermediate Similarity	NPC10225
0.8279	Intermediate Similarity	NPC151197
0.8279	Intermediate Similarity	NPC226629
0.8276	Intermediate Similarity	NPC174981
0.8271	Intermediate Similarity	NPC79622
0.8271	Intermediate Similarity	NPC471183
0.8271	Intermediate Similarity	NPC212942
0.8271	Intermediate Similarity	NPC29868
0.8271	Intermediate Similarity	NPC105847
0.8271	Intermediate Similarity	NPC243759
0.8271	Intermediate Similarity	NPC218131
0.8268	Intermediate Similarity	NPC250432
0.8268	Intermediate Similarity	NPC252131
0.8268	Intermediate Similarity	NPC5447
0.8268	Intermediate Similarity	NPC127587
0.8268	Intermediate Similarity	NPC242032
0.8264	Intermediate Similarity	NPC278652
0.8261	Intermediate Similarity	NPC470700
0.8261	Intermediate Similarity	NPC118286
0.8261	Intermediate Similarity	NPC67250

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 NPC472071 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	917
0.2-0.3	1774
0.3-0.4	3009
0.4-0.5	1583
0.5-0.6	961
0.6-0.7	435
0.7-0.8	60
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8516	High Similarity	NPD1613	Approved
0.8516	High Similarity	NPD1612	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD3027	Phase 3
0.8362	Intermediate Similarity	NPD3021	Approved
0.8362	Intermediate Similarity	NPD3022	Approved
0.8346	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD1242	Phase 1
0.8268	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD940	Approved
0.807	Intermediate Similarity	NPD846	Approved
0.7955	Intermediate Similarity	NPD943	Approved
0.7899	Intermediate Similarity	NPD4750	Phase 3
0.7795	Intermediate Similarity	NPD1610	Phase 2
0.7721	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3094	Phase 2
0.7638	Intermediate Similarity	NPD9381	Approved
0.7638	Intermediate Similarity	NPD9384	Approved
0.7619	Intermediate Similarity	NPD1548	Phase 1
0.7609	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3020	Approved
0.7541	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD3092	Approved
0.7519	Intermediate Similarity	NPD4908	Phase 1
0.748	Intermediate Similarity	NPD228	Approved
0.7478	Intermediate Similarity	NPD2859	Approved
0.7478	Intermediate Similarity	NPD2860	Approved
0.7438	Intermediate Similarity	NPD2342	Discontinued
0.7426	Intermediate Similarity	NPD3062	Approved
0.7426	Intermediate Similarity	NPD3059	Approved
0.7426	Intermediate Similarity	NPD3061	Approved
0.7419	Intermediate Similarity	NPD7635	Approved
0.7414	Intermediate Similarity	NPD288	Approved
0.7407	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD9622	Approved
0.7391	Intermediate Similarity	NPD2933	Approved
0.7391	Intermediate Similarity	NPD2934	Approved
0.7344	Intermediate Similarity	NPD3091	Approved
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7328	Intermediate Similarity	NPD844	Approved
0.7328	Intermediate Similarity	NPD9269	Phase 2
0.7321	Intermediate Similarity	NPD9094	Approved
0.7319	Intermediate Similarity	NPD5314	Approved
0.7313	Intermediate Similarity	NPD3018	Phase 2
0.7292	Intermediate Similarity	NPD1511	Approved
0.728	Intermediate Similarity	NPD9379	Approved
0.728	Intermediate Similarity	NPD9377	Approved
0.7273	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1934	Approved
0.7246	Intermediate Similarity	NPD230	Phase 1
0.7241	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD9619	Approved
0.7239	Intermediate Similarity	NPD9621	Approved
0.7239	Intermediate Similarity	NPD9620	Approved
0.7234	Intermediate Similarity	NPD7266	Discontinued
0.7222	Intermediate Similarity	NPD5283	Phase 1
0.7214	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2568	Approved
0.7192	Intermediate Similarity	NPD1512	Approved
0.7185	Intermediate Similarity	NPD2861	Phase 2
0.7174	Intermediate Similarity	NPD4060	Phase 1
0.7174	Intermediate Similarity	NPD3620	Phase 2
0.7174	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD302	Approved
0.7153	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2983	Phase 2
0.7143	Intermediate Similarity	NPD2982	Phase 2
0.7133	Intermediate Similarity	NPD37	Approved
0.7133	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6234	Discontinued
0.7123	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1201	Approved
0.7099	Intermediate Similarity	NPD3095	Discontinued
0.7095	Intermediate Similarity	NPD1653	Approved
0.7087	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD817	Approved
0.7071	Intermediate Similarity	NPD823	Approved
0.7068	Intermediate Similarity	NPD2981	Phase 2
0.7037	Intermediate Similarity	NPD1470	Approved
0.7037	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1809	Phase 2
0.7034	Intermediate Similarity	NPD6190	Approved
0.7031	Intermediate Similarity	NPD497	Approved
0.7029	Intermediate Similarity	NPD598	Approved
0.7029	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD597	Approved
0.7029	Intermediate Similarity	NPD601	Approved
0.7023	Intermediate Similarity	NPD9268	Approved
0.7015	Intermediate Similarity	NPD4749	Approved
0.7015	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD845	Approved
0.6993	Remote Similarity	NPD4966	Approved
0.6993	Remote Similarity	NPD4965	Approved
0.6993	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4967	Phase 2
0.6978	Remote Similarity	NPD6405	Approved
0.6978	Remote Similarity	NPD6407	Approved
0.6978	Remote Similarity	NPD1136	Approved
0.6978	Remote Similarity	NPD1132	Approved
0.6978	Remote Similarity	NPD1130	Approved
0.6974	Remote Similarity	NPD2801	Approved
0.6974	Remote Similarity	NPD1465	Phase 2
0.6972	Remote Similarity	NPD1510	Phase 2
0.697	Remote Similarity	NPD2286	Discontinued
0.6966	Remote Similarity	NPD3892	Phase 2
0.6963	Remote Similarity	NPD5310	Approved
0.6963	Remote Similarity	NPD5311	Approved
0.6953	Remote Similarity	NPD498	Approved
0.6953	Remote Similarity	NPD495	Approved
0.6953	Remote Similarity	NPD496	Approved
0.6939	Remote Similarity	NPD7390	Discontinued
0.6933	Remote Similarity	NPD4005	Discontinued
0.6929	Remote Similarity	NPD2238	Phase 2
0.6923	Remote Similarity	NPD9570	Approved
0.6923	Remote Similarity	NPD7199	Phase 2
0.6918	Remote Similarity	NPD7228	Approved
0.6912	Remote Similarity	NPD3055	Approved
0.6912	Remote Similarity	NPD3053	Approved
0.6905	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1792	Phase 2
0.6903	Remote Similarity	NPD111	Approved
0.6899	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6166	Phase 2
0.6899	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4093	Discontinued
0.6883	Remote Similarity	NPD3882	Suspended
0.6879	Remote Similarity	NPD6232	Discontinued
0.6866	Remote Similarity	NPD3705	Approved
0.6866	Remote Similarity	NPD422	Phase 1
0.6866	Remote Similarity	NPD1091	Approved
0.6849	Remote Similarity	NPD3750	Approved
0.6842	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2932	Approved
0.6842	Remote Similarity	NPD3019	Approved
0.6842	Remote Similarity	NPD4059	Approved
0.6828	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3818	Discontinued
0.6809	Remote Similarity	NPD1558	Phase 1
0.6809	Remote Similarity	NPD1240	Approved
0.6806	Remote Similarity	NPD5404	Approved
0.6806	Remote Similarity	NPD5406	Approved
0.6806	Remote Similarity	NPD5408	Approved
0.6806	Remote Similarity	NPD5405	Approved
0.6803	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.68	Remote Similarity	NPD968	Approved
0.6797	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD9089	Approved
0.6786	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6674	Discontinued
0.6776	Remote Similarity	NPD4380	Phase 2
0.677	Remote Similarity	NPD5844	Phase 1
0.6759	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3540	Phase 1
0.6759	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7473	Discontinued
0.6746	Remote Similarity	NPD290	Approved
0.6739	Remote Similarity	NPD258	Approved
0.6739	Remote Similarity	NPD859	Approved
0.6739	Remote Similarity	NPD257	Approved
0.6739	Remote Similarity	NPD599	Approved
0.6739	Remote Similarity	NPD858	Approved
0.6739	Remote Similarity	NPD602	Approved
0.6735	Remote Similarity	NPD8166	Discontinued
0.6733	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7074	Phase 3
0.6718	Remote Similarity	NPD709	Approved
0.6718	Remote Similarity	NPD7157	Approved
0.6718	Remote Similarity	NPD6671	Approved
0.6716	Remote Similarity	NPD4626	Approved
0.6716	Remote Similarity	NPD1751	Approved
0.6715	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1607	Approved
0.6712	Remote Similarity	NPD1549	Phase 2
0.6711	Remote Similarity	NPD2421	Approved
0.6711	Remote Similarity	NPD2420	Approved
0.6696	Remote Similarity	NPD9093	Approved
0.6693	Remote Similarity	NPD2684	Approved
0.6692	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2234	Approved
0.6692	Remote Similarity	NPD2229	Approved
0.6692	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2228	Approved
0.6691	Remote Similarity	NPD5736	Approved
0.669	Remote Similarity	NPD3539	Phase 1
0.669	Remote Similarity	NPD1555	Discontinued
0.669	Remote Similarity	NPD825	Approved
0.669	Remote Similarity	NPD826	Approved
0.6689	Remote Similarity	NPD2677	Approved
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD1131	Approved
0.6667	Remote Similarity	NPD1133	Approved
0.6667	Remote Similarity	NPD7325	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