NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	296.05
Volume:	276.931
LogP:	2.062
LogD:	2.289
LogS:	-1.728
# Rotatable Bonds:	4
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.651
Synthetic Accessibility Score:	2.349
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.941
MDCK Permeability:	7.849382200220134e-06
Pgp-inhibitor:	0.019
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	97.77932739257812%
Volume Distribution (VD):	0.432
Pgp-substrate:	2.3071608543395996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.89
CYP1A2-substrate:	0.262
CYP2C19-inhibitor:	0.129
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.62
CYP2D6-inhibitor:	0.7
CYP2D6-substrate:	0.826
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	14.388
Half-life (T1/2):	0.958

ADMET: Toxicity

hERG Blockers:	0.257
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.274
AMES Toxicity:	0.592
Rat Oral Acute Toxicity:	0.459
Maximum Recommended Daily Dose:	0.272
Skin Sensitization:	0.952
Carcinogencity:	0.742
Eye Corrosion:	0.004
Eye Irritation:	0.903
Respiratory Toxicity:	0.074

Download Data

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

Natural Product: NPC193334

Natural Product ID:	NPC193334
*Common Name:**	2-[[3-Chloro-4-Hydroxy-5-(Hydroxymethyl)Phenoxy]Methyl]Benzene-1,4-Diol
IUPAC Name:	2-[[3-chloro-4-hydroxy-5-(hydroxymethyl)phenoxy]methyl]benzene-1,4-diol
Synonyms:
Standard InCHIKey:	WTDORBLYOHYLPZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H13ClO5/c15-12-5-11(4-8(6-16)14(12)19)20-7-9-3-10(17)1-2-13(9)18/h1-5,16-19H,6-7H2
SMILES:	OCc1cc(OCc2cc(O)ccc2O)cc(c1O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402538
PubChem CID:	24770504
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004628] 4-alkoxyphenols

*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
NPO28718	Penicillium terrestre	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163588]
NPO28718	Penicillium terrestre	Species	Aspergillaceae	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
IC50	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	5300.0	nM	PMID[489445]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	5500.0	nM	PMID[489445]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	14300.0	nM	PMID[489445]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	38500.0	nM	PMID[489445]
NPT35	Others	n.a.		IC50	=	4400.0	nM	PMID[489445]

☑ 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 NPC193334 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	568
0.1-0.2	2616
0.2-0.3	10602
0.3-0.4	9450
0.4-0.5	4636
0.5-0.6	9927
0.6-0.7	4549
0.7-0.8	341
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9435	High Similarity	NPC33402
0.888	High Similarity	NPC67791
0.8629	High Similarity	NPC301321
0.8496	Intermediate Similarity	NPC185313
0.8485	Intermediate Similarity	NPC26576
0.8065	Intermediate Similarity	NPC169450
0.7956	Intermediate Similarity	NPC246991
0.792	Intermediate Similarity	NPC241549
0.7902	Intermediate Similarity	NPC252901
0.7868	Intermediate Similarity	NPC8058
0.7863	Intermediate Similarity	NPC283616
0.7846	Intermediate Similarity	NPC290470
0.7846	Intermediate Similarity	NPC154256
0.7786	Intermediate Similarity	NPC139335
0.7778	Intermediate Similarity	NPC261992
0.7704	Intermediate Similarity	NPC188997
0.7692	Intermediate Similarity	NPC470837
0.7674	Intermediate Similarity	NPC474920
0.76	Intermediate Similarity	NPC130817
0.7559	Intermediate Similarity	NPC233320
0.7556	Intermediate Similarity	NPC473875
0.7537	Intermediate Similarity	NPC32152
0.7532	Intermediate Similarity	NPC56379
0.75	Intermediate Similarity	NPC146096
0.75	Intermediate Similarity	NPC40377
0.75	Intermediate Similarity	NPC232165
0.75	Intermediate Similarity	NPC473718
0.7481	Intermediate Similarity	NPC232295
0.7481	Intermediate Similarity	NPC474131
0.7463	Intermediate Similarity	NPC15350
0.7462	Intermediate Similarity	NPC266932
0.7445	Intermediate Similarity	NPC77789
0.7445	Intermediate Similarity	NPC18128
0.7445	Intermediate Similarity	NPC204535
0.7445	Intermediate Similarity	NPC46586
0.7444	Intermediate Similarity	NPC203113
0.7429	Intermediate Similarity	NPC216836
0.7426	Intermediate Similarity	NPC100108
0.7426	Intermediate Similarity	NPC96423
0.7426	Intermediate Similarity	NPC277798
0.7394	Intermediate Similarity	NPC229231
0.7391	Intermediate Similarity	NPC474130
0.7391	Intermediate Similarity	NPC248786
0.7379	Intermediate Similarity	NPC472337
0.7376	Intermediate Similarity	NPC63179
0.7372	Intermediate Similarity	NPC476165
0.7372	Intermediate Similarity	NPC212965
0.7368	Intermediate Similarity	NPC808
0.7361	Intermediate Similarity	NPC138940
0.7339	Intermediate Similarity	NPC88420
0.7333	Intermediate Similarity	NPC74821
0.7329	Intermediate Similarity	NPC472336
0.7329	Intermediate Similarity	NPC476698
0.7329	Intermediate Similarity	NPC472334
0.7328	Intermediate Similarity	NPC255068
0.7328	Intermediate Similarity	NPC275627
0.7324	Intermediate Similarity	NPC45824
0.7324	Intermediate Similarity	NPC97326
0.7323	Intermediate Similarity	NPC474603
0.7323	Intermediate Similarity	NPC12987
0.7319	Intermediate Similarity	NPC27198
0.7319	Intermediate Similarity	NPC151237
0.7319	Intermediate Similarity	NPC120638
0.7319	Intermediate Similarity	NPC302211
0.7313	Intermediate Similarity	NPC69539
0.7313	Intermediate Similarity	NPC163398
0.7313	Intermediate Similarity	NPC150624
0.7305	Intermediate Similarity	NPC50368
0.7299	Intermediate Similarity	NPC475529
0.7292	Intermediate Similarity	NPC15658
0.7292	Intermediate Similarity	NPC219876
0.7292	Intermediate Similarity	NPC126029
0.7292	Intermediate Similarity	NPC261619
0.7292	Intermediate Similarity	NPC185604
0.7292	Intermediate Similarity	NPC78770
0.7292	Intermediate Similarity	NPC61477
0.7292	Intermediate Similarity	NPC273984
0.7292	Intermediate Similarity	NPC161203
0.7292	Intermediate Similarity	NPC66643
0.7287	Intermediate Similarity	NPC194034
0.7286	Intermediate Similarity	NPC167571
0.7286	Intermediate Similarity	NPC133407
0.7286	Intermediate Similarity	NPC28476
0.7286	Intermediate Similarity	NPC131397
0.7286	Intermediate Similarity	NPC476254
0.7286	Intermediate Similarity	NPC207179
0.7286	Intermediate Similarity	NPC278552
0.7279	Intermediate Similarity	NPC471449
0.7279	Intermediate Similarity	NPC121866
0.7279	Intermediate Similarity	NPC51341
0.7279	Intermediate Similarity	NPC295259
0.7273	Intermediate Similarity	NPC214860
0.726	Intermediate Similarity	NPC195022
0.726	Intermediate Similarity	NPC134968
0.7259	Intermediate Similarity	NPC244816
0.7259	Intermediate Similarity	NPC238176
0.7259	Intermediate Similarity	NPC50521
0.7259	Intermediate Similarity	NPC221549
0.7259	Intermediate Similarity	NPC187993
0.7259	Intermediate Similarity	NPC69261
0.7259	Intermediate Similarity	NPC33270
0.7254	Intermediate Similarity	NPC274717
0.7252	Intermediate Similarity	NPC94045
0.7246	Intermediate Similarity	NPC42644
0.7246	Intermediate Similarity	NPC193364
0.7241	Intermediate Similarity	NPC94236
0.7241	Intermediate Similarity	NPC269528
0.7241	Intermediate Similarity	NPC37196
0.7234	Intermediate Similarity	NPC283049
0.7234	Intermediate Similarity	NPC471215
0.7234	Intermediate Similarity	NPC50315
0.7234	Intermediate Similarity	NPC26879
0.7234	Intermediate Similarity	NPC262573
0.7234	Intermediate Similarity	NPC230479
0.7231	Intermediate Similarity	NPC75440
0.723	Intermediate Similarity	NPC471388
0.723	Intermediate Similarity	NPC472151
0.7226	Intermediate Similarity	NPC8283
0.7226	Intermediate Similarity	NPC14177
0.7226	Intermediate Similarity	NPC258979
0.7226	Intermediate Similarity	NPC93398
0.7222	Intermediate Similarity	NPC284232
0.7222	Intermediate Similarity	NPC472590
0.7222	Intermediate Similarity	NPC42760
0.7222	Intermediate Similarity	NPC268342
0.7222	Intermediate Similarity	NPC220825
0.7222	Intermediate Similarity	NPC268266
0.7218	Intermediate Similarity	NPC91452
0.7214	Intermediate Similarity	NPC48990
0.7214	Intermediate Similarity	NPC270030
0.7214	Intermediate Similarity	NPC61685
0.7214	Intermediate Similarity	NPC74478
0.7214	Intermediate Similarity	NPC114901
0.7214	Intermediate Similarity	NPC293701
0.7211	Intermediate Similarity	NPC173660
0.7206	Intermediate Similarity	NPC63010
0.7206	Intermediate Similarity	NPC329980
0.7206	Intermediate Similarity	NPC190514
0.7197	Intermediate Similarity	NPC90520
0.7197	Intermediate Similarity	NPC296920
0.7194	Intermediate Similarity	NPC90577
0.7192	Intermediate Similarity	NPC310854
0.7192	Intermediate Similarity	NPC106215
0.7183	Intermediate Similarity	NPC163332
0.7183	Intermediate Similarity	NPC118787
0.7183	Intermediate Similarity	NPC292056
0.7183	Intermediate Similarity	NPC183181
0.7183	Intermediate Similarity	NPC111247
0.7183	Intermediate Similarity	NPC147821
0.7183	Intermediate Similarity	NPC319625
0.7183	Intermediate Similarity	NPC41706
0.7174	Intermediate Similarity	NPC205213
0.7174	Intermediate Similarity	NPC129176
0.7164	Intermediate Similarity	NPC22610
0.7164	Intermediate Similarity	NPC276737
0.7163	Intermediate Similarity	NPC81641
0.7162	Intermediate Similarity	NPC107551
0.7162	Intermediate Similarity	NPC326797
0.7162	Intermediate Similarity	NPC474282
0.7162	Intermediate Similarity	NPC176051
0.7162	Intermediate Similarity	NPC276490
0.7162	Intermediate Similarity	NPC103976
0.7162	Intermediate Similarity	NPC102904
0.7153	Intermediate Similarity	NPC220935
0.7153	Intermediate Similarity	NPC184302
0.7153	Intermediate Similarity	NPC475880
0.7153	Intermediate Similarity	NPC137294
0.7153	Intermediate Similarity	NPC91291
0.7153	Intermediate Similarity	NPC85895
0.7143	Intermediate Similarity	NPC280606
0.7143	Intermediate Similarity	NPC61946
0.7143	Intermediate Similarity	NPC474160
0.7143	Intermediate Similarity	NPC255147
0.7143	Intermediate Similarity	NPC164787
0.7143	Intermediate Similarity	NPC38761
0.7143	Intermediate Similarity	NPC201357
0.7143	Intermediate Similarity	NPC281521
0.7143	Intermediate Similarity	NPC98372
0.7143	Intermediate Similarity	NPC76465
0.7133	Intermediate Similarity	NPC46274
0.7133	Intermediate Similarity	NPC471389
0.7133	Intermediate Similarity	NPC39064
0.7133	Intermediate Similarity	NPC72529
0.7133	Intermediate Similarity	NPC53986
0.7133	Intermediate Similarity	NPC38664
0.7133	Intermediate Similarity	NPC226331
0.7133	Intermediate Similarity	NPC19694
0.7133	Intermediate Similarity	NPC266691
0.7133	Intermediate Similarity	NPC47283
0.7132	Intermediate Similarity	NPC127894
0.7132	Intermediate Similarity	NPC142042
0.7132	Intermediate Similarity	NPC8302
0.7132	Intermediate Similarity	NPC470759
0.7132	Intermediate Similarity	NPC219070
0.7132	Intermediate Similarity	NPC15860
0.7123	Intermediate Similarity	NPC229442
0.7123	Intermediate Similarity	NPC211352
0.7123	Intermediate Similarity	NPC168059
0.7123	Intermediate Similarity	NPC475840
0.7123	Intermediate Similarity	NPC11060

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 NPC193334 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	434
0.1-0.2	1111
0.2-0.3	2060
0.3-0.4	2618
0.4-0.5	1633
0.5-0.6	999
0.6-0.7	269
0.7-0.8	26
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
0.7905	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD968	Approved
0.7554	Intermediate Similarity	NPD454	Approved
0.75	Intermediate Similarity	NPD6671	Approved
0.7483	Intermediate Similarity	NPD1184	Approved
0.7379	Intermediate Similarity	NPD4538	Approved
0.7379	Intermediate Similarity	NPD4536	Approved
0.7379	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1548	Phase 1
0.7329	Intermediate Similarity	NPD5960	Phase 3
0.7329	Intermediate Similarity	NPD5588	Approved
0.7305	Intermediate Similarity	NPD2861	Phase 2
0.7292	Intermediate Similarity	NPD1613	Approved
0.7292	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD290	Approved
0.7285	Intermediate Similarity	NPD7041	Phase 2
0.7285	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1610	Phase 2
0.719	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3365	Discontinued
0.7174	Intermediate Similarity	NPD915	Approved
0.7174	Intermediate Similarity	NPD3496	Discontinued
0.7154	Intermediate Similarity	NPD9552	Approved
0.7133	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1091	Approved
0.7101	Intermediate Similarity	NPD5846	Approved
0.7101	Intermediate Similarity	NPD6516	Phase 2
0.7086	Intermediate Similarity	NPD4535	Phase 3
0.7063	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9501	Approved
0.7047	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4908	Phase 1
0.7013	Intermediate Similarity	NPD1578	Phase 2
0.6993	Remote Similarity	NPD5058	Phase 3
0.695	Remote Similarity	NPD2231	Phase 2
0.695	Remote Similarity	NPD2235	Phase 2
0.6918	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1416	Approved
0.6879	Remote Similarity	NPD1535	Discovery
0.6879	Remote Similarity	NPD1611	Approved
0.6864	Remote Similarity	NPD3303	Discontinued
0.6849	Remote Similarity	NPD4625	Phase 3
0.6849	Remote Similarity	NPD3027	Phase 3
0.6835	Remote Similarity	NPD1182	Approved
0.6831	Remote Similarity	NPD1157	Approved
0.6831	Remote Similarity	NPD1481	Phase 2
0.6824	Remote Similarity	NPD4060	Phase 1
0.6806	Remote Similarity	NPD1203	Approved
0.6803	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4972	Discontinued
0.6791	Remote Similarity	NPD5451	Approved
0.6783	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4359	Approved
0.6783	Remote Similarity	NPD4749	Approved
0.6781	Remote Similarity	NPD600	Approved
0.6781	Remote Similarity	NPD596	Approved
0.6759	Remote Similarity	NPD6584	Phase 3
0.6757	Remote Similarity	NPD839	Approved
0.6757	Remote Similarity	NPD840	Approved
0.6739	Remote Similarity	NPD191	Approved
0.6738	Remote Similarity	NPD1778	Approved
0.6736	Remote Similarity	NPD3225	Approved
0.6732	Remote Similarity	NPD5958	Discontinued
0.6732	Remote Similarity	NPD4534	Discontinued
0.6716	Remote Similarity	NPD2684	Approved
0.6715	Remote Similarity	NPD1398	Phase 1
0.6711	Remote Similarity	NPD2935	Discontinued
0.6692	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD228	Approved
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD6815	Approved
0.6644	Remote Similarity	NPD558	Phase 2
0.6643	Remote Similarity	NPD422	Phase 1
0.6642	Remote Similarity	NPD7843	Approved
0.6623	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6696	Suspended
0.6619	Remote Similarity	NPD7157	Approved
0.6619	Remote Similarity	NPD709	Approved
0.6605	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1551	Phase 2
0.6597	Remote Similarity	NPD1840	Phase 2
0.6591	Remote Similarity	NPD9500	Approved
0.659	Remote Similarity	NPD3337	Discontinued
0.6581	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2797	Approved
0.6571	Remote Similarity	NPD7340	Approved
0.6565	Remote Similarity	NPD1242	Phase 1
0.6564	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1653	Approved
0.656	Remote Similarity	NPD9295	Approved
0.6558	Remote Similarity	NPD2377	Approved
0.6558	Remote Similarity	NPD2376	Approved
0.6558	Remote Similarity	NPD2378	Approved
0.6556	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6583	Phase 3
0.6552	Remote Similarity	NPD6582	Phase 2
0.6549	Remote Similarity	NPD6382	Discontinued
0.6543	Remote Similarity	NPD958	Approved
0.6538	Remote Similarity	NPD3892	Phase 2
0.6533	Remote Similarity	NPD6233	Phase 2
0.6531	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5894	Phase 2
0.6522	Remote Similarity	NPD821	Approved
0.6503	Remote Similarity	NPD4589	Approved
0.65	Remote Similarity	NPD2557	Approved
0.6494	Remote Similarity	NPD6032	Approved
0.6493	Remote Similarity	NPD9697	Approved
0.6491	Remote Similarity	NPD4873	Discontinued
0.649	Remote Similarity	NPD1555	Discontinued
0.6483	Remote Similarity	NPD9717	Approved
0.6483	Remote Similarity	NPD1608	Approved
0.6483	Remote Similarity	NPD2230	Approved
0.6483	Remote Similarity	NPD2233	Approved
0.6483	Remote Similarity	NPD2232	Approved
0.6479	Remote Similarity	NPD1894	Discontinued
0.6478	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5283	Phase 1
0.6467	Remote Similarity	NPD3268	Approved
0.646	Remote Similarity	NPD957	Approved
0.6457	Remote Similarity	NPD9365	Approved
0.6454	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD447	Suspended
0.6446	Remote Similarity	NPD4064	Discontinued
0.6442	Remote Similarity	NPD3274	Phase 2
0.6438	Remote Similarity	NPD6543	Approved
0.6438	Remote Similarity	NPD6542	Approved
0.6438	Remote Similarity	NPD6540	Phase 3
0.6438	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6539	Approved
0.6438	Remote Similarity	NPD6090	Discontinued
0.6434	Remote Similarity	NPD3445	Approved
0.6434	Remote Similarity	NPD3443	Approved
0.6434	Remote Similarity	NPD3444	Approved
0.6429	Remote Similarity	NPD7033	Discontinued
0.642	Remote Similarity	NPD6057	Approved
0.642	Remote Similarity	NPD6056	Approved
0.6419	Remote Similarity	NPD3691	Phase 2
0.6419	Remote Similarity	NPD3690	Phase 2
0.6416	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6087	Phase 1
0.6415	Remote Similarity	NPD1511	Approved
0.641	Remote Similarity	NPD2808	Discontinued
0.641	Remote Similarity	NPD1549	Phase 2
0.6405	Remote Similarity	NPD6653	Approved
0.6403	Remote Similarity	NPD769	Approved
0.6403	Remote Similarity	NPD5535	Approved
0.6403	Remote Similarity	NPD7635	Approved
0.64	Remote Similarity	NPD1024	Discontinued
0.6395	Remote Similarity	NPD6538	Approved
0.6395	Remote Similarity	NPD6541	Approved
0.6395	Remote Similarity	NPD3933	Discontinued
0.6395	Remote Similarity	NPD5095	Phase 3
0.6395	Remote Similarity	NPD5096	Phase 3
0.6392	Remote Similarity	NPD2354	Approved
0.6391	Remote Similarity	NPD291	Approved
0.6389	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD844	Approved
0.6383	Remote Similarity	NPD9685	Approved
0.6382	Remote Similarity	NPD2238	Phase 2
0.638	Remote Similarity	NPD1714	Approved
0.638	Remote Similarity	NPD1715	Phase 1
0.638	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD1712	Approved
0.6376	Remote Similarity	NPD3018	Phase 2
0.6375	Remote Similarity	NPD2504	Approved
0.6375	Remote Similarity	NPD2505	Approved
0.6369	Remote Similarity	NPD5177	Phase 3
0.6364	Remote Similarity	NPD2801	Approved
0.6358	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD411	Approved
0.6358	Remote Similarity	NPD6798	Discontinued
0.6358	Remote Similarity	NPD1048	Approved
0.6351	Remote Similarity	NPD987	Approved
0.6346	Remote Similarity	NPD5763	Approved
0.6346	Remote Similarity	NPD5762	Approved
0.6343	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6355	Discontinued
0.6336	Remote Similarity	NPD288	Approved
0.6335	Remote Similarity	NPD1512	Approved
0.6333	Remote Similarity	NPD6832	Phase 2
0.6329	Remote Similarity	NPD1718	Discontinued
0.6325	Remote Similarity	NPD5402	Approved
0.6323	Remote Similarity	NPD2156	Approved
0.6323	Remote Similarity	NPD3260	Discontinued
0.6323	Remote Similarity	NPD2155	Approved
0.6323	Remote Similarity	NPD1510	Phase 2
0.6323	Remote Similarity	NPD2154	Approved
0.6323	Remote Similarity	NPD4308	Phase 3
0.6319	Remote Similarity	NPD1357	Approved
0.6319	Remote Similarity	NPD3049	Approved
0.6319	Remote Similarity	NPD3769	Discontinued
0.6319	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7477	Discontinued

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