NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	270.459
LogP:	2.054
LogD:	1.841
LogS:	-3.236
# Rotatable Bonds:	1
TPSA:	83.81
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	2.946
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.874
MDCK Permeability:	2.3448665160685778e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.656

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	79.45018768310547%
Volume Distribution (VD):	1.084
Pgp-substrate:	14.832077980041504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.84
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.37
CYP2C9-substrate:	0.372
CYP2D6-inhibitor:	0.489
CYP2D6-substrate:	0.296
CYP3A4-inhibitor:	0.255
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	10.219
Half-life (T1/2):	0.69

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.306
Rat Oral Acute Toxicity:	0.629
Maximum Recommended Daily Dose:	0.79
Skin Sensitization:	0.499
Carcinogencity:	0.936
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.415

Download Data

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

Natural Product: NPC19860

Natural Product ID:	NPC19860
*Common Name:**	8-Methyl-11-Hydroxyl-12-Isopropanol-Furancoumarin
IUPAC Name:	3-hydroxy-2-(2-hydroxypropan-2-yl)-9-methylfuro[3,2-g]chromen-7-one
Synonyms:
Standard InCHIKey:	SVDKENTVUOEKSX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O5/c1-7-12-8(4-5-10(16)19-12)6-9-11(17)14(15(2,3)18)20-13(7)9/h4-6,17-18H,1-3H3
SMILES:	O=c1ccc2c(o1)c(C)c1c(c2)c(c(o1)C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1956007
PubChem CID:	57345578
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens

*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
NPO33397	tetramorium sp.	Species	Formicidae	Eukaryota	n.a.	ChangBai Mountain, China	n.a.	PMID[22364815]

☑ 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
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	4.0	mm	PMID[517485]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[517485]

☑ 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 NPC19860 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	384
0.1-0.2	1900
0.2-0.3	4691
0.3-0.4	10991
0.4-0.5	7070
0.5-0.6	4275
0.6-0.7	6168
0.7-0.8	4344
0.8-0.85	2196
0.85-0.9	641
0.9-0.95	36
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9236	High Similarity	NPC15819
0.9211	High Similarity	NPC98028
0.9177	High Similarity	NPC204088
0.9177	High Similarity	NPC259007
0.9177	High Similarity	NPC329215
0.9074	High Similarity	NPC233956
0.9068	High Similarity	NPC281835
0.9	High Similarity	NPC323137
0.8951	High Similarity	NPC51404
0.8924	High Similarity	NPC169
0.891	High Similarity	NPC469934
0.891	High Similarity	NPC279218
0.891	High Similarity	NPC108937
0.8868	High Similarity	NPC14822
0.8867	High Similarity	NPC254010
0.8861	High Similarity	NPC33320
0.8859	High Similarity	NPC262635
0.8854	High Similarity	NPC321372
0.8854	High Similarity	NPC474609
0.8854	High Similarity	NPC474738
0.8854	High Similarity	NPC109967
0.8854	High Similarity	NPC475797
0.8854	High Similarity	NPC469936
0.8854	High Similarity	NPC78554
0.8854	High Similarity	NPC129053
0.8854	High Similarity	NPC472461
0.8831	High Similarity	NPC37208
0.8831	High Similarity	NPC221868
0.8812	High Similarity	NPC219861
0.8808	High Similarity	NPC313036
0.8805	High Similarity	NPC303210
0.8805	High Similarity	NPC49009
0.8805	High Similarity	NPC243509
0.8805	High Similarity	NPC95472
0.8805	High Similarity	NPC239270
0.8774	High Similarity	NPC155882
0.8766	High Similarity	NPC272194
0.8766	High Similarity	NPC211811
0.8758	High Similarity	NPC210826
0.875	High Similarity	NPC216092
0.875	High Similarity	NPC225884
0.8735	High Similarity	NPC107244
0.8726	High Similarity	NPC475895
0.8726	High Similarity	NPC131725
0.8726	High Similarity	NPC189130
0.8725	High Similarity	NPC332594
0.8704	High Similarity	NPC173149
0.8704	High Similarity	NPC179015
0.8701	High Similarity	NPC129650
0.8701	High Similarity	NPC140120
0.8701	High Similarity	NPC12148
0.8701	High Similarity	NPC180477
0.8701	High Similarity	NPC130581
0.8696	High Similarity	NPC272722
0.8693	High Similarity	NPC1886
0.8693	High Similarity	NPC196137
0.8693	High Similarity	NPC469953
0.8684	High Similarity	NPC36181
0.8684	High Similarity	NPC53192
0.8679	High Similarity	NPC270044
0.8679	High Similarity	NPC210048
0.8679	High Similarity	NPC269495
0.8675	High Similarity	NPC28337
0.8675	High Similarity	NPC224165
0.8675	High Similarity	NPC53917
0.8671	High Similarity	NPC234255
0.8671	High Similarity	NPC472280
0.8662	High Similarity	NPC285623
0.8662	High Similarity	NPC304954
0.8662	High Similarity	NPC237994
0.8662	High Similarity	NPC327269
0.8662	High Similarity	NPC31627
0.8662	High Similarity	NPC476238
0.8654	High Similarity	NPC470908
0.8654	High Similarity	NPC472421
0.8654	High Similarity	NPC260582
0.8654	High Similarity	NPC321387
0.8654	High Similarity	NPC327059
0.8645	High Similarity	NPC135325
0.8645	High Similarity	NPC208303
0.8645	High Similarity	NPC161864
0.8642	High Similarity	NPC179464
0.8642	High Similarity	NPC1706
0.8642	High Similarity	NPC39305
0.8642	High Similarity	NPC59295
0.8642	High Similarity	NPC472581
0.8642	High Similarity	NPC1755
0.8642	High Similarity	NPC263092
0.8636	High Similarity	NPC51641
0.8636	High Similarity	NPC300267
0.8636	High Similarity	NPC181388
0.8636	High Similarity	NPC470322
0.8636	High Similarity	NPC154217
0.8636	High Similarity	NPC57470
0.8627	High Similarity	NPC87609
0.8627	High Similarity	NPC94794
0.8627	High Similarity	NPC302181
0.8627	High Similarity	NPC188632
0.8627	High Similarity	NPC470296
0.8627	High Similarity	NPC112791
0.8627	High Similarity	NPC196459
0.8625	High Similarity	NPC264932
0.8625	High Similarity	NPC311574
0.8625	High Similarity	NPC16935
0.8625	High Similarity	NPC244750
0.8616	High Similarity	NPC6633
0.8616	High Similarity	NPC5322
0.8616	High Similarity	NPC472455
0.8616	High Similarity	NPC133970
0.8608	High Similarity	NPC472462
0.8606	High Similarity	NPC120220
0.86	High Similarity	NPC221046
0.8599	High Similarity	NPC474744
0.8599	High Similarity	NPC472423
0.8599	High Similarity	NPC474772
0.8599	High Similarity	NPC472580
0.8599	High Similarity	NPC471675
0.8599	High Similarity	NPC290671
0.8599	High Similarity	NPC154345
0.8591	High Similarity	NPC151113
0.859	High Similarity	NPC469932
0.859	High Similarity	NPC37226
0.859	High Similarity	NPC226644
0.859	High Similarity	NPC296030
0.859	High Similarity	NPC39929
0.859	High Similarity	NPC88445
0.8589	High Similarity	NPC36320
0.8581	High Similarity	NPC140840
0.8581	High Similarity	NPC74539
0.8581	High Similarity	NPC249942
0.8581	High Similarity	NPC304443
0.8581	High Similarity	NPC86847
0.8581	High Similarity	NPC297886
0.8581	High Similarity	NPC202494
0.858	High Similarity	NPC8300
0.858	High Similarity	NPC234536
0.858	High Similarity	NPC238995
0.858	High Similarity	NPC78612
0.8571	High Similarity	NPC178627
0.8571	High Similarity	NPC230943
0.8571	High Similarity	NPC115432
0.8571	High Similarity	NPC98546
0.8571	High Similarity	NPC316535
0.8571	High Similarity	NPC297807
0.8571	High Similarity	NPC172687
0.8571	High Similarity	NPC328102
0.8571	High Similarity	NPC260296
0.8571	High Similarity	NPC297788
0.8571	High Similarity	NPC469935
0.8562	High Similarity	NPC51146
0.8562	High Similarity	NPC166858
0.8562	High Similarity	NPC473042
0.8562	High Similarity	NPC474681
0.8562	High Similarity	NPC161650
0.8562	High Similarity	NPC218313
0.8562	High Similarity	NPC162476
0.8554	High Similarity	NPC472584
0.8553	High Similarity	NPC200246
0.8553	High Similarity	NPC250769
0.8553	High Similarity	NPC278010
0.8553	High Similarity	NPC221173
0.8553	High Similarity	NPC295608
0.8544	High Similarity	NPC477957
0.8544	High Similarity	NPC55205
0.8544	High Similarity	NPC256141
0.8544	High Similarity	NPC157784
0.8544	High Similarity	NPC63187
0.8544	High Similarity	NPC41326
0.8544	High Similarity	NPC473996
0.8544	High Similarity	NPC37684
0.8543	High Similarity	NPC183639
0.8543	High Similarity	NPC199458
0.8537	High Similarity	NPC155264
0.8537	High Similarity	NPC193881
0.8537	High Similarity	NPC67450
0.8537	High Similarity	NPC210460
0.8535	High Similarity	NPC116822
0.8535	High Similarity	NPC151973
0.8535	High Similarity	NPC230713
0.8535	High Similarity	NPC180351
0.8535	High Similarity	NPC191104
0.8535	High Similarity	NPC78335
0.8528	High Similarity	NPC472582
0.8528	High Similarity	NPC234004
0.8528	High Similarity	NPC155640
0.8526	High Similarity	NPC469933
0.8526	High Similarity	NPC19545
0.8526	High Similarity	NPC266743
0.8519	High Similarity	NPC92589
0.8519	High Similarity	NPC188486
0.8519	High Similarity	NPC94155
0.8516	High Similarity	NPC124729
0.8516	High Similarity	NPC220418
0.8512	High Similarity	NPC164384
0.8509	High Similarity	NPC196879
0.8509	High Similarity	NPC74178
0.8509	High Similarity	NPC204879
0.8509	High Similarity	NPC184755
0.8506	High Similarity	NPC293053
0.8506	High Similarity	NPC212932

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 NPC19860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	990
0.2-0.3	1797
0.3-0.4	2724
0.4-0.5	1855
0.5-0.6	979
0.6-0.7	302
0.7-0.8	90
0.8-0.85	36
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8861	High Similarity	NPD919	Approved
0.8859	High Similarity	NPD1243	Approved
0.8581	High Similarity	NPD920	Approved
0.8562	High Similarity	NPD643	Clinical (unspecified phase)
0.8562	High Similarity	NPD7075	Discontinued
0.85	High Similarity	NPD3882	Suspended
0.8491	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD3749	Approved
0.8428	Intermediate Similarity	NPD6801	Discontinued
0.8397	Intermediate Similarity	NPD1512	Approved
0.8387	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD1247	Approved
0.8269	Intermediate Similarity	NPD1511	Approved
0.821	Intermediate Similarity	NPD3817	Phase 2
0.8199	Intermediate Similarity	NPD1934	Approved
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8148	Intermediate Similarity	NPD2801	Approved
0.8148	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1510	Phase 2
0.8079	Intermediate Similarity	NPD1240	Approved
0.8075	Intermediate Similarity	NPD4380	Phase 2
0.8065	Intermediate Similarity	NPD1549	Phase 2
0.8047	Intermediate Similarity	NPD3818	Discontinued
0.8025	Intermediate Similarity	NPD7411	Suspended
0.8013	Intermediate Similarity	NPD2800	Approved
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1607	Approved
0.7965	Intermediate Similarity	NPD6559	Discontinued
0.7962	Intermediate Similarity	NPD3750	Approved
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6166	Phase 2
0.7927	Intermediate Similarity	NPD1465	Phase 2
0.7927	Intermediate Similarity	NPD7819	Suspended
0.7895	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5403	Approved
0.7885	Intermediate Similarity	NPD2344	Approved
0.7875	Intermediate Similarity	NPD5401	Approved
0.787	Intermediate Similarity	NPD3926	Phase 2
0.7831	Intermediate Similarity	NPD7768	Phase 2
0.7824	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2796	Approved
0.7821	Intermediate Similarity	NPD1551	Phase 2
0.7816	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7733	Intermediate Similarity	NPD1203	Approved
0.7725	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2313	Discontinued
0.7701	Intermediate Similarity	NPD6797	Phase 2
0.7692	Intermediate Similarity	NPD5494	Approved
0.7688	Intermediate Similarity	NPD2309	Approved
0.7688	Intermediate Similarity	NPD5844	Phase 1
0.7688	Intermediate Similarity	NPD7054	Approved
0.7677	Intermediate Similarity	NPD447	Suspended
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5402	Approved
0.7665	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7251	Discontinued
0.7651	Intermediate Similarity	NPD9717	Approved
0.7644	Intermediate Similarity	NPD7472	Approved
0.7644	Intermediate Similarity	NPD7074	Phase 3
0.7643	Intermediate Similarity	NPD2799	Discontinued
0.7643	Intermediate Similarity	NPD3748	Approved
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7808	Phase 3
0.7613	Intermediate Similarity	NPD943	Approved
0.7595	Intermediate Similarity	NPD2935	Discontinued
0.7584	Intermediate Similarity	NPD422	Phase 1
0.7556	Intermediate Similarity	NPD4287	Approved
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3226	Approved
0.7455	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD230	Phase 1
0.7438	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4308	Phase 3
0.7405	Intermediate Similarity	NPD6651	Approved
0.7405	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5049	Phase 3
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7362	Intermediate Similarity	NPD2354	Approved
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7341	Intermediate Similarity	NPD6959	Discontinued
0.7329	Intermediate Similarity	NPD1471	Phase 3
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1296	Phase 2
0.7261	Intermediate Similarity	NPD3268	Approved
0.7261	Intermediate Similarity	NPD411	Approved
0.7257	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7233	Intermediate Similarity	NPD5124	Phase 1
0.7233	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1933	Approved
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.7205	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD5711	Approved
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4307	Phase 2
0.7169	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1164	Approved
0.7161	Intermediate Similarity	NPD2797	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.7151	Intermediate Similarity	NPD1729	Discontinued
0.7151	Intermediate Similarity	NPD2296	Approved
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7117	Intermediate Similarity	NPD2353	Approved
0.7117	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1653	Approved
0.7097	Intermediate Similarity	NPD3225	Approved
0.7086	Intermediate Similarity	NPD9545	Approved
0.7078	Intermediate Similarity	NPD1608	Approved
0.707	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD9493	Approved
0.7052	Intermediate Similarity	NPD4288	Approved
0.7051	Intermediate Similarity	NPD3267	Approved
0.7051	Intermediate Similarity	NPD3266	Approved
0.7044	Intermediate Similarity	NPD6798	Discontinued
0.7039	Intermediate Similarity	NPD3751	Discontinued
0.7029	Intermediate Similarity	NPD6234	Discontinued
0.7022	Intermediate Similarity	NPD2403	Approved
0.7019	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2798	Approved
0.7006	Intermediate Similarity	NPD1019	Discontinued
0.6968	Remote Similarity	NPD9269	Phase 2
0.6962	Remote Similarity	NPD9494	Approved
0.6959	Remote Similarity	NPD7458	Discontinued
0.6957	Remote Similarity	NPD1613	Approved
0.6957	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4060	Phase 1
0.6951	Remote Similarity	NPD5405	Approved
0.6951	Remote Similarity	NPD6100	Approved
0.6951	Remote Similarity	NPD6099	Approved
0.6951	Remote Similarity	NPD5408	Approved
0.6951	Remote Similarity	NPD5404	Approved
0.6951	Remote Similarity	NPD5406	Approved
0.6946	Remote Similarity	NPD6190	Approved
0.6946	Remote Similarity	NPD3887	Approved
0.6928	Remote Similarity	NPD1652	Phase 2
0.6928	Remote Similarity	NPD2654	Approved
0.6927	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6585	Discontinued
0.6918	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7229	Phase 3
0.691	Remote Similarity	NPD6808	Phase 2
0.6903	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4361	Phase 2
0.6895	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7584	Approved
0.6883	Remote Similarity	NPD17	Approved
0.6864	Remote Similarity	NPD7390	Discontinued
0.6863	Remote Similarity	NPD1548	Phase 1
0.6851	Remote Similarity	NPD2163	Approved
0.6839	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD37	Approved
0.6836	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7435	Discontinued
0.6821	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4966	Approved
0.6818	Remote Similarity	NPD4965	Approved
0.6818	Remote Similarity	NPD4967	Phase 2
0.6816	Remote Similarity	NPD3787	Discontinued
0.6811	Remote Similarity	NPD8312	Approved
0.6811	Remote Similarity	NPD8313	Approved
0.6807	Remote Similarity	NPD6004	Phase 3
0.6807	Remote Similarity	NPD6002	Phase 3
0.6807	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6005	Phase 3
0.6807	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1610	Phase 2
0.6793	Remote Similarity	NPD7685	Pre-registration
0.6791	Remote Similarity	NPD8150	Discontinued
0.679	Remote Similarity	NPD6233	Phase 2
0.6786	Remote Similarity	NPD7003	Approved
0.6782	Remote Similarity	NPD5889	Approved
0.6782	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5890	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