NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.08
Volume:	241.503
LogP:	2.873
LogD:	2.629
LogS:	-3.205
# Rotatable Bonds:	3
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.793
Synthetic Accessibility Score:	2.019
Fsp3:	0.071
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:	-4.663
MDCK Permeability:	1.0627931260387413e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.081
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.276

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	95.7927017211914%
Volume Distribution (VD):	0.501
Pgp-substrate:	2.9906983375549316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.821
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.86
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.756
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.692
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.489
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	12.17
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.304
AMES Toxicity:	0.562
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.715
Carcinogencity:	0.767
Eye Corrosion:	0.491
Eye Irritation:	0.985
Respiratory Toxicity:	0.561

Download Data

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

Natural Product: NPC184527

Natural Product ID:	NPC184527
*Common Name:**	Forkienin
IUPAC Name:	2-hydroxy-5-[(4-hydroxyphenyl)methyl]benzaldehyde
Synonyms:	forkienin
Standard InCHIKey:	OOIJRRBPTUCNMW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O3/c15-9-12-8-11(3-6-14(12)17)7-10-1-4-13(16)5-2-10/h1-6,8-9,16-17H,7H2
SMILES:	O=Cc1cc(ccc1O)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376251
PubChem CID:	16109788
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
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO22423	Microtropis fokienensis	Species	Celastraceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	276000.0	nM	PMID[523796]

☑ 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 NPC184527 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	316
0.1-0.2	1725
0.2-0.3	4428
0.3-0.4	12490
0.4-0.5	6191
0.5-0.6	6664
0.6-0.7	8007
0.7-0.8	2617
0.8-0.85	214
0.85-0.9	40
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9224	High Similarity	NPC216216
0.9145	High Similarity	NPC295034
0.9	High Similarity	NPC303264
0.8862	High Similarity	NPC476119
0.8829	High Similarity	NPC141523
0.8803	High Similarity	NPC249435
0.875	High Similarity	NPC224584
0.872	High Similarity	NPC85342
0.8718	High Similarity	NPC174087
0.8696	High Similarity	NPC242136
0.8684	High Similarity	NPC114682
0.8667	High Similarity	NPC156139
0.8621	High Similarity	NPC285350
0.8618	High Similarity	NPC62952
0.8609	High Similarity	NPC228988
0.8595	High Similarity	NPC32032
0.8595	High Similarity	NPC133909
0.8584	High Similarity	NPC17525
0.8583	High Similarity	NPC297186
0.8571	High Similarity	NPC275504
0.8571	High Similarity	NPC41847
0.8571	High Similarity	NPC475042
0.8571	High Similarity	NPC473767
0.8548	High Similarity	NPC105157
0.8548	High Similarity	NPC190043
0.8548	High Similarity	NPC98254
0.8548	High Similarity	NPC30501
0.8548	High Similarity	NPC100067
0.8548	High Similarity	NPC23126
0.8548	High Similarity	NPC266689
0.8548	High Similarity	NPC162612
0.8548	High Similarity	NPC169250
0.8548	High Similarity	NPC103356
0.8548	High Similarity	NPC72158
0.8547	High Similarity	NPC23402
0.8534	High Similarity	NPC211421
0.8512	High Similarity	NPC267552
0.8512	High Similarity	NPC45438
0.8512	High Similarity	NPC196976
0.8512	High Similarity	NPC242895
0.8512	High Similarity	NPC143427
0.8512	High Similarity	NPC224273
0.8512	High Similarity	NPC115159
0.8512	High Similarity	NPC19174
0.8512	High Similarity	NPC73532
0.85	High Similarity	NPC233282
0.8492	Intermediate Similarity	NPC245395
0.8487	Intermediate Similarity	NPC41567
0.8487	Intermediate Similarity	NPC283844
0.8482	Intermediate Similarity	NPC219913
0.848	Intermediate Similarity	NPC21305
0.848	Intermediate Similarity	NPC473017
0.848	Intermediate Similarity	NPC221777
0.8468	Intermediate Similarity	NPC267846
0.8462	Intermediate Similarity	NPC163154
0.8443	Intermediate Similarity	NPC283514
0.8443	Intermediate Similarity	NPC309765
0.8443	Intermediate Similarity	NPC300274
0.8438	Intermediate Similarity	NPC40524
0.8438	Intermediate Similarity	NPC139074
0.8438	Intermediate Similarity	NPC213485
0.8438	Intermediate Similarity	NPC52407
0.8435	Intermediate Similarity	NPC116842
0.8435	Intermediate Similarity	NPC252544
0.8435	Intermediate Similarity	NPC321252
0.8417	Intermediate Similarity	NPC182240
0.8417	Intermediate Similarity	NPC188814
0.8417	Intermediate Similarity	NPC195262
0.8413	Intermediate Similarity	NPC99731
0.8413	Intermediate Similarity	NPC474998
0.8413	Intermediate Similarity	NPC102829
0.8413	Intermediate Similarity	NPC120488
0.8413	Intermediate Similarity	NPC474546
0.8407	Intermediate Similarity	NPC69332
0.8407	Intermediate Similarity	NPC95178
0.8407	Intermediate Similarity	NPC29989
0.84	Intermediate Similarity	NPC116513
0.839	Intermediate Similarity	NPC322197
0.839	Intermediate Similarity	NPC161304
0.8374	Intermediate Similarity	NPC375356
0.8362	Intermediate Similarity	NPC268388
0.8362	Intermediate Similarity	NPC212718
0.8362	Intermediate Similarity	NPC177576
0.8361	Intermediate Similarity	NPC198336
0.8361	Intermediate Similarity	NPC303737
0.8348	Intermediate Similarity	NPC88141
0.8348	Intermediate Similarity	NPC95172
0.8347	Intermediate Similarity	NPC216297
0.8347	Intermediate Similarity	NPC159525
0.8347	Intermediate Similarity	NPC7151
0.8347	Intermediate Similarity	NPC473662
0.8346	Intermediate Similarity	NPC136588
0.8346	Intermediate Similarity	NPC199253
0.8333	Intermediate Similarity	NPC3009
0.8333	Intermediate Similarity	NPC474890
0.8333	Intermediate Similarity	NPC161943
0.8333	Intermediate Similarity	NPC273282
0.8333	Intermediate Similarity	NPC226699
0.832	Intermediate Similarity	NPC136342
0.832	Intermediate Similarity	NPC49647
0.832	Intermediate Similarity	NPC295202
0.832	Intermediate Similarity	NPC8745
0.832	Intermediate Similarity	NPC227741
0.8308	Intermediate Similarity	NPC61153
0.8308	Intermediate Similarity	NPC470210
0.8308	Intermediate Similarity	NPC283590
0.8308	Intermediate Similarity	NPC70859
0.8308	Intermediate Similarity	NPC130899
0.8306	Intermediate Similarity	NPC173978
0.8306	Intermediate Similarity	NPC142956
0.8306	Intermediate Similarity	NPC234890
0.8306	Intermediate Similarity	NPC74507
0.8306	Intermediate Similarity	NPC68756
0.8306	Intermediate Similarity	NPC152525
0.8306	Intermediate Similarity	NPC236189
0.8306	Intermediate Similarity	NPC13238
0.8293	Intermediate Similarity	NPC307174
0.8291	Intermediate Similarity	NPC286222
0.8281	Intermediate Similarity	NPC244699
0.8264	Intermediate Similarity	NPC161617
0.8264	Intermediate Similarity	NPC158222
0.8261	Intermediate Similarity	NPC100551
0.8258	Intermediate Similarity	NPC206207
0.825	Intermediate Similarity	NPC230349
0.825	Intermediate Similarity	NPC28169
0.8246	Intermediate Similarity	NPC6984
0.8246	Intermediate Similarity	NPC70843
0.824	Intermediate Similarity	NPC10926
0.824	Intermediate Similarity	NPC131799
0.824	Intermediate Similarity	NPC103540
0.8235	Intermediate Similarity	NPC240163
0.823	Intermediate Similarity	NPC8931
0.823	Intermediate Similarity	NPC261573
0.823	Intermediate Similarity	NPC120693
0.822	Intermediate Similarity	NPC11824
0.8217	Intermediate Similarity	NPC70622
0.8211	Intermediate Similarity	NPC215392
0.8203	Intermediate Similarity	NPC31799
0.8203	Intermediate Similarity	NPC62219
0.8197	Intermediate Similarity	NPC206778
0.8197	Intermediate Similarity	NPC285829
0.8195	Intermediate Similarity	NPC471620
0.8189	Intermediate Similarity	NPC48248
0.8189	Intermediate Similarity	NPC282923
0.8189	Intermediate Similarity	NPC95537
0.8182	Intermediate Similarity	NPC94637
0.8182	Intermediate Similarity	NPC283711
0.8175	Intermediate Similarity	NPC160499
0.8175	Intermediate Similarity	NPC473751
0.8175	Intermediate Similarity	NPC96915
0.8174	Intermediate Similarity	NPC228737
0.8167	Intermediate Similarity	NPC108288
0.8167	Intermediate Similarity	NPC477453
0.8167	Intermediate Similarity	NPC128825
0.8167	Intermediate Similarity	NPC83718
0.816	Intermediate Similarity	NPC184219
0.8158	Intermediate Similarity	NPC163734
0.8154	Intermediate Similarity	NPC314048
0.8154	Intermediate Similarity	NPC53896
0.8151	Intermediate Similarity	NPC276111
0.8151	Intermediate Similarity	NPC118288
0.8148	Intermediate Similarity	NPC73061
0.8145	Intermediate Similarity	NPC91105
0.8145	Intermediate Similarity	NPC67300
0.8145	Intermediate Similarity	NPC244351
0.8145	Intermediate Similarity	NPC68167
0.8142	Intermediate Similarity	NPC470202
0.814	Intermediate Similarity	NPC93015
0.814	Intermediate Similarity	NPC474517
0.814	Intermediate Similarity	NPC72669
0.8125	Intermediate Similarity	NPC146647
0.8125	Intermediate Similarity	NPC34414
0.812	Intermediate Similarity	NPC141368
0.812	Intermediate Similarity	NPC21162
0.8115	Intermediate Similarity	NPC201284
0.8115	Intermediate Similarity	NPC328459
0.8115	Intermediate Similarity	NPC90522
0.811	Intermediate Similarity	NPC22783
0.811	Intermediate Similarity	NPC473787
0.8106	Intermediate Similarity	NPC131039
0.8103	Intermediate Similarity	NPC317305
0.8099	Intermediate Similarity	NPC269414
0.8099	Intermediate Similarity	NPC121259
0.8095	Intermediate Similarity	NPC4164
0.8092	Intermediate Similarity	NPC282780
0.8092	Intermediate Similarity	NPC166480
0.8092	Intermediate Similarity	NPC50924
0.8091	Intermediate Similarity	NPC286006
0.8087	Intermediate Similarity	NPC188677
0.808	Intermediate Similarity	NPC472029
0.808	Intermediate Similarity	NPC174991
0.808	Intermediate Similarity	NPC65761
0.8077	Intermediate Similarity	NPC313618
0.8074	Intermediate Similarity	NPC187843
0.8067	Intermediate Similarity	NPC53953
0.8065	Intermediate Similarity	NPC226275
0.8065	Intermediate Similarity	NPC120545
0.8062	Intermediate Similarity	NPC31539
0.806	Intermediate Similarity	NPC19622
0.806	Intermediate Similarity	NPC112789

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 NPC184527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	1008
0.2-0.3	1261
0.3-0.4	2791
0.4-0.5	2073
0.5-0.6	1207
0.6-0.7	411
0.7-0.8	70
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8689	High Similarity	NPD1164	Approved
0.8361	Intermediate Similarity	NPD1201	Approved
0.8261	Intermediate Similarity	NPD9266	Approved
0.8261	Intermediate Similarity	NPD74	Approved
0.824	Intermediate Similarity	NPD1470	Approved
0.8174	Intermediate Similarity	NPD9267	Approved
0.8174	Intermediate Similarity	NPD9264	Approved
0.8174	Intermediate Similarity	NPD9263	Approved
0.8167	Intermediate Similarity	NPD9493	Approved
0.8167	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1240	Approved
0.8045	Intermediate Similarity	NPD2935	Discontinued
0.797	Intermediate Similarity	NPD1510	Phase 2
0.7967	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD1607	Approved
0.7939	Intermediate Similarity	NPD943	Approved
0.792	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD1237	Approved
0.7863	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD9261	Approved
0.7812	Intermediate Similarity	NPD1203	Approved
0.7794	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD5408	Approved
0.7778	Intermediate Similarity	NPD5404	Approved
0.7778	Intermediate Similarity	NPD5406	Approved
0.7778	Intermediate Similarity	NPD5405	Approved
0.7742	Intermediate Similarity	NPD9545	Approved
0.7721	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD9281	Approved
0.7704	Intermediate Similarity	NPD2799	Discontinued
0.7652	Intermediate Similarity	NPD2313	Discontinued
0.7647	Intermediate Similarity	NPD1551	Phase 2
0.7615	Intermediate Similarity	NPD2798	Approved
0.7611	Intermediate Similarity	NPD2859	Approved
0.7611	Intermediate Similarity	NPD2860	Approved
0.7591	Intermediate Similarity	NPD2344	Approved
0.7589	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD2933	Approved
0.7522	Intermediate Similarity	NPD2934	Approved
0.7482	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD520	Approved
0.7448	Intermediate Similarity	NPD4380	Phase 2
0.7442	Intermediate Similarity	NPD9717	Approved
0.7414	Intermediate Similarity	NPD3020	Approved
0.7388	Intermediate Similarity	NPD3764	Approved
0.7376	Intermediate Similarity	NPD2309	Approved
0.7368	Intermediate Similarity	NPD6832	Phase 2
0.7343	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD1241	Discontinued
0.7338	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3972	Approved
0.7305	Intermediate Similarity	NPD7003	Approved
0.7304	Intermediate Similarity	NPD1809	Phase 2
0.7293	Intermediate Similarity	NPD9494	Approved
0.7281	Intermediate Similarity	NPD845	Approved
0.7279	Intermediate Similarity	NPD7411	Suspended
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7266	Intermediate Similarity	NPD2796	Approved
0.7227	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1930	Approved
0.7227	Intermediate Similarity	NPD1929	Approved
0.7214	Intermediate Similarity	NPD2346	Discontinued
0.7213	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2932	Approved
0.7209	Intermediate Similarity	NPD3019	Approved
0.7203	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7768	Phase 2
0.7197	Intermediate Similarity	NPD1283	Approved
0.7197	Intermediate Similarity	NPD1876	Approved
0.7194	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD9256	Approved
0.7168	Intermediate Similarity	NPD9258	Approved
0.7152	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD5951	Approved
0.7143	Intermediate Similarity	NPD846	Approved
0.7143	Intermediate Similarity	NPD940	Approved
0.7133	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1202	Approved
0.7119	Intermediate Similarity	NPD1238	Approved
0.7103	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD256	Approved
0.7087	Intermediate Similarity	NPD255	Approved
0.7069	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7819	Suspended
0.7063	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3400	Discontinued
0.7063	Intermediate Similarity	NPD3750	Approved
0.7054	Intermediate Similarity	NPD1894	Discontinued
0.7045	Intermediate Similarity	NPD1481	Phase 2
0.7042	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4208	Discontinued
0.7034	Intermediate Similarity	NPD1511	Approved
0.7034	Intermediate Similarity	NPD6799	Approved
0.7027	Intermediate Similarity	NPD111	Approved
0.7027	Intermediate Similarity	NPD7458	Discontinued
0.7015	Intermediate Similarity	NPD2797	Approved
0.7009	Intermediate Similarity	NPD844	Approved
0.7007	Intermediate Similarity	NPD920	Approved
0.7	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD6801	Discontinued
0.7	Intermediate Similarity	NPD1934	Approved
0.6992	Remote Similarity	NPD2342	Discontinued
0.6978	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1281	Approved
0.697	Remote Similarity	NPD1535	Discovery
0.6966	Remote Similarity	NPD3300	Phase 2
0.6963	Remote Similarity	NPD1019	Discontinued
0.695	Remote Similarity	NPD4308	Phase 3
0.6949	Remote Similarity	NPD288	Approved
0.6944	Remote Similarity	NPD4628	Phase 3
0.6944	Remote Similarity	NPD1196	Approved
0.6939	Remote Similarity	NPD1512	Approved
0.6929	Remote Similarity	NPD6651	Approved
0.6928	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1543	Discontinued
0.6917	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1242	Phase 1
0.6913	Remote Similarity	NPD3226	Approved
0.6905	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4476	Approved
0.6901	Remote Similarity	NPD4477	Approved
0.6899	Remote Similarity	NPD9568	Approved
0.6897	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD9495	Approved
0.6884	Remote Similarity	NPD411	Approved
0.6884	Remote Similarity	NPD6798	Discontinued
0.688	Remote Similarity	NPD3022	Approved
0.688	Remote Similarity	NPD3021	Approved
0.6879	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1243	Approved
0.6875	Remote Similarity	NPD1195	Approved
0.6871	Remote Similarity	NPD4662	Approved
0.6871	Remote Similarity	NPD4661	Approved
0.6867	Remote Similarity	NPD6599	Discontinued
0.6863	Remote Similarity	NPD3882	Suspended
0.6857	Remote Similarity	NPD1933	Approved
0.6857	Remote Similarity	NPD447	Suspended
0.685	Remote Similarity	NPD7635	Approved
0.6838	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6663	Approved
0.6832	Remote Similarity	NPD6559	Discontinued
0.6818	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4626	Approved
0.6814	Remote Similarity	NPD9257	Approved
0.6814	Remote Similarity	NPD9259	Approved
0.68	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2296	Approved
0.6797	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1548	Phase 1
0.6794	Remote Similarity	NPD1759	Phase 1
0.6794	Remote Similarity	NPD5304	Approved
0.6794	Remote Similarity	NPD5303	Approved
0.6791	Remote Similarity	NPD9269	Phase 2
0.6788	Remote Similarity	NPD5736	Approved
0.678	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5403	Approved
0.6774	Remote Similarity	NPD968	Approved
0.6767	Remote Similarity	NPD3847	Discontinued
0.6763	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3268	Approved
0.6759	Remote Similarity	NPD2800	Approved
0.6757	Remote Similarity	NPD2532	Approved
0.6757	Remote Similarity	NPD2533	Approved
0.6757	Remote Similarity	NPD2534	Approved
0.6757	Remote Similarity	NPD5401	Approved
0.6752	Remote Similarity	NPD6232	Discontinued
0.6742	Remote Similarity	NPD9268	Approved
0.6741	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5157	Phase 1
0.6741	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5159	Phase 2
0.6741	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4207	Discontinued
0.6738	Remote Similarity	NPD6355	Discontinued
0.6738	Remote Similarity	NPD230	Phase 1
0.6736	Remote Similarity	NPD1471	Phase 3
0.6735	Remote Similarity	NPD7440	Discontinued
0.6732	Remote Similarity	NPD2801	Approved
0.6721	Remote Similarity	NPD1932	Approved
0.6718	Remote Similarity	NPD1758	Phase 1
0.6716	Remote Similarity	NPD1610	Phase 2
0.6713	Remote Similarity	NPD3748	Approved
0.6713	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD8166	Discontinued
0.6711	Remote Similarity	NPD5049	Phase 3
0.6711	Remote Similarity	NPD6273	Approved
0.671	Remote Similarity	NPD3749	Approved
0.6694	Remote Similarity	NPD2066	Phase 3
0.6692	Remote Similarity	NPD4589	Approved
0.6691	Remote Similarity	NPD7008	Discontinued
0.6691	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD4060	Phase 1

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