NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.09
Volume:	244.139
LogP:	3.075
LogD:	3.209
LogS:	-4.072
# Rotatable Bonds:	3
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.88
Synthetic Accessibility Score:	1.578
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.657
MDCK Permeability:	2.5884806746034883e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.321
Plasma Protein Binding (PPB):	96.91221618652344%
Volume Distribution (VD):	0.779
Pgp-substrate:	2.539867877960205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.864
CYP2C19-substrate:	0.459
CYP2C9-inhibitor:	0.593
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.16
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.359
CYP3A4-substrate:	0.477

ADMET: Excretion

Clearance (CL):	10.318
Half-life (T1/2):	0.841

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.176
AMES Toxicity:	0.152
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.067
Skin Sensitization:	0.943
Carcinogencity:	0.33
Eye Corrosion:	0.228
Eye Irritation:	0.89
Respiratory Toxicity:	0.215

Download Data

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

Natural Product: NPC5796

Natural Product ID:	NPC5796
*Common Name:**	Aucuparin
IUPAC Name:	2,6-dimethoxy-4-phenylphenol
Synonyms:	Aucuparin
Standard InCHIKey:	KCKBEANTNJGRCV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O3/c1-16-12-8-11(9-13(17-2)14(12)15)10-6-4-3-5-7-10/h3-9,15H,1-2H3
SMILES:	COc1cc(cc(c1O)OC)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079777
PubChem CID:	442508
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives

*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
NPO13029	Sorbus aucuparia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18635332]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19813743]
NPO10507	Sorbus decora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20738101]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	trunk	Jeju island, Korea	2005-Dec	PMID[21420296]
NPO3204	Centaurea malacitana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358646]
NPO13029	Sorbus aucuparia	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13029	Sorbus aucuparia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10507	Sorbus decora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13029	Sorbus aucuparia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13029	Sorbus aucuparia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13408	Cordeauxia edulis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3628	Solanum aethiopicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3204	Centaurea malacitana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14617	Aloe hijazensis	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10507	Sorbus decora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13029	Sorbus aucuparia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6180	Ocotea puberula	Species	Lauraceae	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
Others	3

Activity Type	# Activity
Cell Line	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[555537]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[555537]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[555537]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PMID[555537]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	116.96	%	PMID[555538]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	125.76	%	PMID[555538]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	50150.0	nM	PMID[555538]
NPT27	Others	Unspecified		Activity	=	126.19	%	PMID[555538]

☑ 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 NPC5796 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	471
0.1-0.2	1875
0.2-0.3	5701
0.3-0.4	13401
0.4-0.5	3715
0.5-0.6	4421
0.6-0.7	7685
0.7-0.8	4027
0.8-0.85	735
0.85-0.9	455
0.9-0.95	172
0.95-1	39

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC206487
0.975	High Similarity	NPC266555
0.9746	High Similarity	NPC84086
0.9669	High Similarity	NPC154866
0.9661	High Similarity	NPC41562
0.9587	High Similarity	NPC127587
0.9583	High Similarity	NPC233410
0.9583	High Similarity	NPC251855
0.9583	High Similarity	NPC57490
0.9583	High Similarity	NPC298757
0.9583	High Similarity	NPC203133
0.9583	High Similarity	NPC116907
0.9583	High Similarity	NPC117214
0.9583	High Similarity	NPC193544
0.9583	High Similarity	NPC221077
0.9583	High Similarity	NPC475169
0.9583	High Similarity	NPC17943
0.9583	High Similarity	NPC208950
0.9583	High Similarity	NPC472093
0.958	High Similarity	NPC197757
0.958	High Similarity	NPC228922
0.9504	High Similarity	NPC223953
0.9504	High Similarity	NPC76451
0.9487	High Similarity	NPC20674
0.9426	High Similarity	NPC124452
0.9426	High Similarity	NPC74817
0.9426	High Similarity	NPC324112
0.9426	High Similarity	NPC236791
0.9426	High Similarity	NPC169474
0.9426	High Similarity	NPC159968
0.9426	High Similarity	NPC82679
0.9426	High Similarity	NPC246620
0.9426	High Similarity	NPC293054
0.9426	High Similarity	NPC282000
0.9421	High Similarity	NPC234400
0.9421	High Similarity	NPC60885
0.9417	High Similarity	NPC136319
0.9417	High Similarity	NPC233526
0.9417	High Similarity	NPC282496
0.9407	High Similarity	NPC61516
0.9407	High Similarity	NPC10932
0.9407	High Similarity	NPC232084
0.9407	High Similarity	NPC247364
0.9355	High Similarity	NPC126836
0.935	High Similarity	NPC206615
0.935	High Similarity	NPC470213
0.935	High Similarity	NPC98631
0.935	High Similarity	NPC186843
0.9344	High Similarity	NPC214406
0.9344	High Similarity	NPC78974
0.9344	High Similarity	NPC223136
0.9344	High Similarity	NPC28730
0.9344	High Similarity	NPC103823
0.9344	High Similarity	NPC18924
0.9344	High Similarity	NPC44748
0.9333	High Similarity	NPC71579
0.9333	High Similarity	NPC262253
0.9333	High Similarity	NPC473411
0.9322	High Similarity	NPC226629
0.9322	High Similarity	NPC15805
0.9316	High Similarity	NPC259638
0.9316	High Similarity	NPC195466
0.9286	High Similarity	NPC32778
0.928	High Similarity	NPC474356
0.928	High Similarity	NPC45715
0.928	High Similarity	NPC12275
0.928	High Similarity	NPC474017
0.9274	High Similarity	NPC170844
0.9274	High Similarity	NPC476968
0.9268	High Similarity	NPC210355
0.9262	High Similarity	NPC105925
0.9262	High Similarity	NPC299584
0.9262	High Similarity	NPC82483
0.9262	High Similarity	NPC265483
0.9256	High Similarity	NPC121115
0.9231	High Similarity	NPC193067
0.9213	High Similarity	NPC160697
0.9206	High Similarity	NPC6451
0.92	High Similarity	NPC299221
0.92	High Similarity	NPC311680
0.92	High Similarity	NPC51840
0.92	High Similarity	NPC234488
0.9194	High Similarity	NPC28765
0.918	High Similarity	NPC122792
0.918	High Similarity	NPC228972
0.9167	High Similarity	NPC166759
0.9145	High Similarity	NPC167934
0.9141	High Similarity	NPC10314
0.9141	High Similarity	NPC108198
0.9141	High Similarity	NPC256262
0.9141	High Similarity	NPC158142
0.9141	High Similarity	NPC294884
0.9141	High Similarity	NPC200557
0.9141	High Similarity	NPC69029
0.9134	High Similarity	NPC158331
0.9127	High Similarity	NPC232275
0.912	High Similarity	NPC10225
0.912	High Similarity	NPC190144
0.912	High Similarity	NPC212015
0.912	High Similarity	NPC58164
0.9113	High Similarity	NPC252131
0.9113	High Similarity	NPC236760
0.9113	High Similarity	NPC470699
0.9098	High Similarity	NPC95168
0.9091	High Similarity	NPC49341
0.9091	High Similarity	NPC145780
0.9083	High Similarity	NPC474565
0.9083	High Similarity	NPC229401
0.907	High Similarity	NPC143139
0.907	High Similarity	NPC202846
0.9068	High Similarity	NPC141090
0.9062	High Similarity	NPC469659
0.9062	High Similarity	NPC188378
0.9062	High Similarity	NPC276026
0.9062	High Similarity	NPC287745
0.9062	High Similarity	NPC56764
0.9062	High Similarity	NPC555
0.9062	High Similarity	NPC289258
0.9062	High Similarity	NPC206737
0.9062	High Similarity	NPC7515
0.9062	High Similarity	NPC125649
0.9055	High Similarity	NPC175067
0.9055	High Similarity	NPC14224
0.9055	High Similarity	NPC86655
0.9055	High Similarity	NPC253105
0.9055	High Similarity	NPC204215
0.9055	High Similarity	NPC201587
0.9055	High Similarity	NPC161958
0.9055	High Similarity	NPC202762
0.9048	High Similarity	NPC224157
0.9048	High Similarity	NPC192687
0.9048	High Similarity	NPC472338
0.904	High Similarity	NPC266691
0.9032	High Similarity	NPC181361
0.9	High Similarity	NPC310338
0.9	High Similarity	NPC242715
0.9	High Similarity	NPC272157
0.9	High Similarity	NPC475961
0.9	High Similarity	NPC254625
0.9	High Similarity	NPC266453
0.9	High Similarity	NPC56329
0.9	High Similarity	NPC6262
0.9	High Similarity	NPC200935
0.9	High Similarity	NPC90615
0.9	High Similarity	NPC281298
0.9	High Similarity	NPC25111
0.9	High Similarity	NPC230919
0.9	High Similarity	NPC201145
0.9	High Similarity	NPC151656
0.9	High Similarity	NPC73535
0.8992	High Similarity	NPC293619
0.8992	High Similarity	NPC313081
0.8992	High Similarity	NPC474933
0.8992	High Similarity	NPC214853
0.8992	High Similarity	NPC221549
0.8992	High Similarity	NPC126409
0.8992	High Similarity	NPC240279
0.8992	High Similarity	NPC180602
0.8992	High Similarity	NPC50521
0.8992	High Similarity	NPC55239
0.8992	High Similarity	NPC99572
0.8992	High Similarity	NPC244816
0.8992	High Similarity	NPC241241
0.8984	High Similarity	NPC475840
0.8976	High Similarity	NPC472597
0.8976	High Similarity	NPC470096
0.8976	High Similarity	NPC15543
0.8976	High Similarity	NPC470095
0.896	High Similarity	NPC165045
0.896	High Similarity	NPC5428
0.896	High Similarity	NPC118533
0.896	High Similarity	NPC106511
0.896	High Similarity	NPC21563
0.8952	High Similarity	NPC148627
0.8943	High Similarity	NPC471693
0.8943	High Similarity	NPC220598
0.8943	High Similarity	NPC165375
0.8934	High Similarity	NPC285289
0.8934	High Similarity	NPC75713
0.8934	High Similarity	NPC477886
0.8931	High Similarity	NPC132804
0.8931	High Similarity	NPC55947
0.8931	High Similarity	NPC105847
0.8931	High Similarity	NPC220344
0.8931	High Similarity	NPC243996
0.8931	High Similarity	NPC212942
0.8931	High Similarity	NPC243759
0.8931	High Similarity	NPC79622
0.8931	High Similarity	NPC29868
0.8931	High Similarity	NPC275061
0.8931	High Similarity	NPC22517
0.8931	High Similarity	NPC218131
0.8926	High Similarity	NPC95614
0.8926	High Similarity	NPC165133
0.8926	High Similarity	NPC232316
0.8926	High Similarity	NPC242885
0.8926	High Similarity	NPC227217
0.8926	High Similarity	NPC117780
0.8926	High Similarity	NPC56214
0.8923	High Similarity	NPC133025

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 NPC5796 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	439
0.1-0.2	975
0.2-0.3	1760
0.3-0.4	2751
0.4-0.5	1598
0.5-0.6	910
0.6-0.7	590
0.7-0.8	111
0.8-0.85	12
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9274	High Similarity	NPD3027	Phase 3
0.8889	High Similarity	NPD1529	Clinical (unspecified phase)
0.881	High Similarity	NPD1530	Clinical (unspecified phase)
0.8803	High Similarity	NPD228	Approved
0.876	High Similarity	NPD1612	Clinical (unspecified phase)
0.876	High Similarity	NPD1613	Approved
0.8347	Intermediate Similarity	NPD5283	Phase 1
0.8346	Intermediate Similarity	NPD2982	Phase 2
0.8346	Intermediate Similarity	NPD2983	Phase 2
0.8333	Intermediate Similarity	NPD1610	Phase 2
0.8268	Intermediate Similarity	NPD2981	Phase 2
0.8231	Intermediate Similarity	NPD3018	Phase 2
0.816	Intermediate Similarity	NPD1548	Phase 1
0.8062	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD1558	Phase 1
0.803	Intermediate Similarity	NPD4908	Phase 1
0.8017	Intermediate Similarity	NPD3021	Approved
0.8017	Intermediate Similarity	NPD3022	Approved
0.797	Intermediate Similarity	NPD4625	Phase 3
0.7949	Intermediate Similarity	NPD1242	Phase 1
0.791	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD1934	Approved
0.7794	Intermediate Similarity	NPD3620	Phase 2
0.7794	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4749	Approved
0.7651	Intermediate Similarity	NPD2801	Approved
0.7639	Intermediate Similarity	NPD1511	Approved
0.7634	Intermediate Similarity	NPD422	Phase 1
0.7622	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD3540	Phase 1
0.7583	Intermediate Similarity	NPD846	Approved
0.7583	Intermediate Similarity	NPD940	Approved
0.7569	Intermediate Similarity	NPD7124	Phase 2
0.7566	Intermediate Similarity	NPD6234	Discontinued
0.7556	Intermediate Similarity	NPD2861	Phase 2
0.755	Intermediate Similarity	NPD3882	Suspended
0.7538	Intermediate Similarity	NPD1357	Approved
0.7536	Intermediate Similarity	NPD1240	Approved
0.7534	Intermediate Similarity	NPD1512	Approved
0.7533	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD9296	Approved
0.7519	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5536	Phase 2
0.7518	Intermediate Similarity	NPD3539	Phase 1
0.7518	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4357	Discontinued
0.75	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD2684	Approved
0.75	Intermediate Similarity	NPD6111	Discontinued
0.75	Intermediate Similarity	NPD4005	Discontinued
0.7467	Intermediate Similarity	NPD37	Approved
0.7464	Intermediate Similarity	NPD2674	Phase 3
0.744	Intermediate Similarity	NPD4750	Phase 3
0.7432	Intermediate Similarity	NPD1653	Approved
0.7429	Intermediate Similarity	NPD1607	Approved
0.7426	Intermediate Similarity	NPD9494	Approved
0.7419	Intermediate Similarity	NPD6232	Discontinued
0.7417	Intermediate Similarity	NPD3020	Approved
0.7417	Intermediate Similarity	NPD1465	Phase 2
0.741	Intermediate Similarity	NPD4060	Phase 1
0.7364	Intermediate Similarity	NPD7157	Approved
0.7361	Intermediate Similarity	NPD3060	Approved
0.7357	Intermediate Similarity	NPD230	Phase 1
0.7339	Intermediate Similarity	NPD968	Approved
0.7333	Intermediate Similarity	NPD1283	Approved
0.7333	Intermediate Similarity	NPD4678	Approved
0.7333	Intermediate Similarity	NPD4675	Approved
0.7325	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6166	Phase 2
0.7325	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1510	Phase 2
0.732	Intermediate Similarity	NPD4965	Approved
0.732	Intermediate Similarity	NPD4967	Phase 2
0.732	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4966	Approved
0.7313	Intermediate Similarity	NPD1608	Approved
0.7311	Intermediate Similarity	NPD2860	Approved
0.7311	Intermediate Similarity	NPD2859	Approved
0.7297	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD943	Approved
0.728	Intermediate Similarity	NPD290	Approved
0.7279	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7473	Discontinued
0.7273	Intermediate Similarity	NPD4055	Discovery
0.7273	Intermediate Similarity	NPD1651	Approved
0.7266	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD5109	Approved
0.7266	Intermediate Similarity	NPD3144	Approved
0.7266	Intermediate Similarity	NPD3145	Approved
0.7266	Intermediate Similarity	NPD5111	Phase 2
0.7266	Intermediate Similarity	NPD7843	Approved
0.7266	Intermediate Similarity	NPD5110	Phase 2
0.726	Intermediate Similarity	NPD2219	Phase 1
0.7259	Intermediate Similarity	NPD1669	Approved
0.7248	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7199	Phase 2
0.7233	Intermediate Similarity	NPD7228	Approved
0.7231	Intermediate Similarity	NPD709	Approved
0.7231	Intermediate Similarity	NPD6671	Approved
0.7227	Intermediate Similarity	NPD2933	Approved
0.7227	Intermediate Similarity	NPD2934	Approved
0.7226	Intermediate Similarity	NPD6584	Phase 3
0.7222	Intermediate Similarity	NPD7266	Discontinued
0.7222	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7095	Approved
0.7181	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5451	Approved
0.7163	Intermediate Similarity	NPD2238	Phase 2
0.7161	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6100	Approved
0.7153	Intermediate Similarity	NPD6099	Approved
0.7152	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7125	Intermediate Similarity	NPD3818	Discontinued
0.7123	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4237	Approved
0.7123	Intermediate Similarity	NPD4236	Phase 3
0.7123	Intermediate Similarity	NPD5177	Phase 3
0.7122	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1091	Approved
0.7111	Intermediate Similarity	NPD1281	Approved
0.7103	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1375	Discontinued
0.7103	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD17	Approved
0.709	Intermediate Similarity	NPD2667	Approved
0.709	Intermediate Similarity	NPD2668	Approved
0.709	Intermediate Similarity	NPD5846	Approved
0.709	Intermediate Similarity	NPD4626	Approved
0.709	Intermediate Similarity	NPD6516	Phase 2
0.7083	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5844	Phase 1
0.7081	Intermediate Similarity	NPD7054	Approved
0.708	Intermediate Similarity	NPD8651	Approved
0.7075	Intermediate Similarity	NPD3750	Approved
0.7075	Intermediate Similarity	NPD6331	Phase 2
0.7059	Intermediate Similarity	NPD2233	Approved
0.7059	Intermediate Similarity	NPD2232	Approved
0.7059	Intermediate Similarity	NPD2230	Approved
0.7055	Intermediate Similarity	NPD1549	Phase 2
0.7042	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7472	Approved
0.7032	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8053	Approved
0.703	Intermediate Similarity	NPD8054	Approved
0.7027	Intermediate Similarity	NPD5241	Discontinued
0.7021	Intermediate Similarity	NPD5718	Phase 2
0.7016	Intermediate Similarity	NPD291	Approved
0.7014	Intermediate Similarity	NPD4538	Approved
0.7014	Intermediate Similarity	NPD6896	Approved
0.7014	Intermediate Similarity	NPD6895	Approved
0.7014	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4536	Approved
0.7009	Intermediate Similarity	NPD9094	Approved
0.7007	Intermediate Similarity	NPD6674	Discontinued
0.7007	Intermediate Similarity	NPD6582	Phase 2
0.7007	Intermediate Similarity	NPD6583	Phase 3
0.7	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9379	Approved
0.7	Intermediate Similarity	NPD7447	Phase 1
0.7	Intermediate Similarity	NPD9377	Approved
0.7	Intermediate Similarity	NPD4123	Phase 3
0.6993	Remote Similarity	NPD4380	Phase 2
0.6993	Remote Similarity	NPD5735	Approved
0.6978	Remote Similarity	NPD4624	Approved
0.6977	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2978	Approved
0.6968	Remote Similarity	NPD2977	Approved
0.6967	Remote Similarity	NPD288	Approved
0.6966	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD9381	Approved
0.6963	Remote Similarity	NPD9384	Approved
0.6959	Remote Similarity	NPD3892	Phase 2
0.6959	Remote Similarity	NPD4110	Phase 3
0.6959	Remote Similarity	NPD4628	Phase 3
0.6959	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2922	Phase 1
0.6948	Remote Similarity	NPD5090	Approved
0.6948	Remote Similarity	NPD5089	Approved
0.6944	Remote Similarity	NPD4097	Suspended
0.6935	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7213	Phase 3
0.6933	Remote Similarity	NPD7212	Phase 2
0.6928	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2935	Discontinued
0.6918	Remote Similarity	NPD2161	Phase 2
0.6913	Remote Similarity	NPD6190	Approved
0.6912	Remote Similarity	NPD3847	Discontinued
0.6892	Remote Similarity	NPD1652	Phase 2
0.6892	Remote Similarity	NPD4162	Approved
0.689	Remote Similarity	NPD6797	Phase 2
0.6887	Remote Similarity	NPD1424	Approved
0.6887	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD844	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