NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.05
Volume:	265.186
LogP:	2.804
LogD:	1.868
LogS:	-3.944
# Rotatable Bonds:	1
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.309
Synthetic Accessibility Score:	2.651
Fsp3:	0.0
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:	-5.29
MDCK Permeability:	4.819796231458895e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.941
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	96.54800415039062%
Volume Distribution (VD):	0.485
Pgp-substrate:	5.901763439178467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.37
CYP2C9-substrate:	0.463
CYP2D6-inhibitor:	0.272
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.167
CYP3A4-substrate:	0.038

ADMET: Excretion

Clearance (CL):	7.634
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.613
AMES Toxicity:	0.618
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.948
Carcinogencity:	0.073
Eye Corrosion:	0.019
Eye Irritation:	0.932
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC52407

Natural Product ID:	NPC52407
*Common Name:**	1,7-Dihydroxy-3-Hydroxymethyl-9,10-Anthraquinone
IUPAC Name:	1,7-dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	NWPULPMOTUPXPI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O5/c16-6-7-3-11-13(12(18)4-7)15(20)10-5-8(17)1-2-9(10)14(11)19/h1-5,16-18H,6H2
SMILES:	c1cc2c(cc1O)C(=O)c1c(cc(cc1O)CO)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229891
PubChem CID:	76311504
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO32651	trichoderma harzianum strain th-r16	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19650641]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	6

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	GI	=	92.8	%	PMID[503770]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	GI	=	67.3	%	PMID[503770]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	220700.0	nM	PMID[503770]
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	<	10.0	mm	PMID[503770]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	14.33	mm	PMID[503770]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	<	10.0	mm	PMID[503770]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	<	10.0	mm	PMID[503770]

☑ 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 NPC52407 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	378
0.1-0.2	1684
0.2-0.3	3749
0.3-0.4	10005
0.4-0.5	8988
0.5-0.6	5422
0.6-0.7	7533
0.7-0.8	4374
0.8-0.85	381
0.85-0.9	133
0.9-0.95	45
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC199253
0.9762	High Similarity	NPC136588
0.9609	High Similarity	NPC70622
0.9531	High Similarity	NPC93015
0.9453	High Similarity	NPC31799
0.9398	High Similarity	NPC190457
0.9237	High Similarity	NPC314048
0.9225	High Similarity	NPC99731
0.9206	High Similarity	NPC375356
0.9167	High Similarity	NPC50924
0.9147	High Similarity	NPC282923
0.9141	High Similarity	NPC96915
0.9134	High Similarity	NPC142956
0.9127	High Similarity	NPC300274
0.9127	High Similarity	NPC91478
0.9118	High Similarity	NPC305845
0.9118	High Similarity	NPC204045
0.9104	High Similarity	NPC53414
0.9104	High Similarity	NPC53206
0.9098	High Similarity	NPC80035
0.9098	High Similarity	NPC258502
0.9091	High Similarity	NPC225051
0.9091	High Similarity	NPC294226
0.9084	High Similarity	NPC205992
0.9062	High Similarity	NPC103540
0.9058	High Similarity	NPC471906
0.9058	High Similarity	NPC244691
0.9051	High Similarity	NPC73061
0.9051	High Similarity	NPC135524
0.9048	High Similarity	NPC120545
0.9037	High Similarity	NPC4214
0.9037	High Similarity	NPC13715
0.9037	High Similarity	NPC61398
0.9037	High Similarity	NPC416
0.903	High Similarity	NPC155211
0.903	High Similarity	NPC254847
0.9023	High Similarity	NPC288089
0.9023	High Similarity	NPC202225
0.9023	High Similarity	NPC44437
0.9	High Similarity	NPC48248
0.8984	High Similarity	NPC152525
0.8984	High Similarity	NPC68756
0.8971	High Similarity	NPC143438
0.8971	High Similarity	NPC242994
0.8971	High Similarity	NPC138099
0.8963	High Similarity	NPC471905
0.8955	High Similarity	NPC283088
0.8947	High Similarity	NPC53896
0.8939	High Similarity	NPC471851
0.8939	High Similarity	NPC244699
0.8931	High Similarity	NPC146647
0.8931	High Similarity	NPC34414
0.8929	High Similarity	NPC314437
0.8921	High Similarity	NPC193703
0.8921	High Similarity	NPC21599
0.8921	High Similarity	NPC79627
0.8913	High Similarity	NPC469520
0.8913	High Similarity	NPC474961
0.8905	High Similarity	NPC181560
0.8905	High Similarity	NPC169452
0.8889	High Similarity	NPC315275
0.8865	High Similarity	NPC119767
0.8864	High Similarity	NPC55949
0.8857	High Similarity	NPC478019
0.8849	High Similarity	NPC66593
0.8841	High Similarity	NPC290550
0.8837	High Similarity	NPC173978
0.8837	High Similarity	NPC234890
0.8837	High Similarity	NPC74507
0.8832	High Similarity	NPC26924
0.8828	High Similarity	NPC307174
0.8824	High Similarity	NPC305060
0.8824	High Similarity	NPC147418
0.8806	High Similarity	NPC115458
0.8806	High Similarity	NPC267205
0.8797	High Similarity	NPC85342
0.8794	High Similarity	NPC147250
0.8786	High Similarity	NPC48762
0.8777	High Similarity	NPC19631
0.8777	High Similarity	NPC85310
0.8777	High Similarity	NPC193555
0.8777	High Similarity	NPC239136
0.8768	High Similarity	NPC315578
0.875	High Similarity	NPC272268
0.875	High Similarity	NPC474813
0.874	High Similarity	NPC7151
0.874	High Similarity	NPC473662
0.874	High Similarity	NPC216297
0.8723	High Similarity	NPC34482
0.8722	High Similarity	NPC198305
0.8722	High Similarity	NPC108129
0.8712	High Similarity	NPC247250
0.8712	High Similarity	NPC234175
0.8712	High Similarity	NPC767
0.8712	High Similarity	NPC96024
0.8705	High Similarity	NPC246638
0.8702	High Similarity	NPC160499
0.8702	High Similarity	NPC3224
0.8692	High Similarity	NPC310540
0.8686	High Similarity	NPC245923
0.8686	High Similarity	NPC475957
0.8681	High Similarity	NPC147735
0.8681	High Similarity	NPC255641
0.8681	High Similarity	NPC290954
0.8667	High Similarity	NPC78307
0.8662	High Similarity	NPC470570
0.8662	High Similarity	NPC300540
0.8657	High Similarity	NPC72669
0.8657	High Similarity	NPC474517
0.8657	High Similarity	NPC41847
0.8647	High Similarity	NPC276238
0.8643	High Similarity	NPC137649
0.8643	High Similarity	NPC69755
0.8643	High Similarity	NPC257644
0.8636	High Similarity	NPC69424
0.8636	High Similarity	NPC176130
0.8636	High Similarity	NPC78364
0.8636	High Similarity	NPC84672
0.8633	High Similarity	NPC96421
0.8633	High Similarity	NPC183345
0.8633	High Similarity	NPC203063
0.8623	High Similarity	NPC173980
0.8613	High Similarity	NPC86524
0.8613	High Similarity	NPC191976
0.8603	High Similarity	NPC282780
0.8603	High Similarity	NPC166480
0.8601	High Similarity	NPC478018
0.8594	High Similarity	NPC206778
0.8594	High Similarity	NPC285829
0.8593	High Similarity	NPC110609
0.8593	High Similarity	NPC242358
0.8593	High Similarity	NPC58685
0.8593	High Similarity	NPC246693
0.8583	High Similarity	NPC41567
0.8582	High Similarity	NPC27659
0.8582	High Similarity	NPC31539
0.8582	High Similarity	NPC147757
0.8582	High Similarity	NPC238629
0.8582	High Similarity	NPC471682
0.8582	High Similarity	NPC117609
0.8571	High Similarity	NPC237225
0.8571	High Similarity	NPC95537
0.8571	High Similarity	NPC124365
0.8571	High Similarity	NPC187843
0.8571	High Similarity	NPC477275
0.8561	High Similarity	NPC1268
0.8561	High Similarity	NPC114620
0.8561	High Similarity	NPC103337
0.8561	High Similarity	NPC231774
0.8561	High Similarity	NPC306765
0.8561	High Similarity	NPC254492
0.855	High Similarity	NPC199273
0.854	High Similarity	NPC161632
0.8538	High Similarity	NPC282577
0.8531	High Similarity	NPC285122
0.8531	High Similarity	NPC143685
0.8529	High Similarity	NPC171968
0.8529	High Similarity	NPC59459
0.8529	High Similarity	NPC477139
0.8527	High Similarity	NPC472046
0.8521	High Similarity	NPC48130
0.8521	High Similarity	NPC300684
0.8521	High Similarity	NPC218866
0.8521	High Similarity	NPC84568
0.8507	High Similarity	NPC278928
0.8503	High Similarity	NPC474824
0.8503	High Similarity	NPC470408
0.8503	High Similarity	NPC182921
0.8503	High Similarity	NPC218870
0.85	High Similarity	NPC471853
0.8496	Intermediate Similarity	NPC72667
0.8493	Intermediate Similarity	NPC118427
0.8493	Intermediate Similarity	NPC470569
0.8489	Intermediate Similarity	NPC206207
0.8483	Intermediate Similarity	NPC478219
0.8478	Intermediate Similarity	NPC474311
0.8478	Intermediate Similarity	NPC141934
0.8472	Intermediate Similarity	NPC472135
0.8472	Intermediate Similarity	NPC312929
0.8472	Intermediate Similarity	NPC289042
0.8472	Intermediate Similarity	NPC118027
0.8472	Intermediate Similarity	NPC56433
0.8472	Intermediate Similarity	NPC290194
0.8472	Intermediate Similarity	NPC245584
0.8472	Intermediate Similarity	NPC190648
0.8472	Intermediate Similarity	NPC126767
0.8472	Intermediate Similarity	NPC37709
0.8462	Intermediate Similarity	NPC73416
0.8462	Intermediate Similarity	NPC295034
0.8462	Intermediate Similarity	NPC160777
0.8462	Intermediate Similarity	NPC471683
0.8462	Intermediate Similarity	NPC170055
0.8456	Intermediate Similarity	NPC17843
0.8456	Intermediate Similarity	NPC478190
0.8456	Intermediate Similarity	NPC309430
0.8451	Intermediate Similarity	NPC53016
0.844	Intermediate Similarity	NPC110810
0.844	Intermediate Similarity	NPC91019
0.844	Intermediate Similarity	NPC106519
0.8438	Intermediate Similarity	NPC184527

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 NPC52407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	962
0.2-0.3	1414
0.3-0.4	2773
0.4-0.5	2025
0.5-0.6	1108
0.6-0.7	400
0.7-0.8	92
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9062	High Similarity	NPD1470	Approved
0.903	High Similarity	NPD1509	Clinical (unspecified phase)
0.875	High Similarity	NPD1201	Approved
0.8425	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD5406	Approved
0.8286	Intermediate Similarity	NPD5404	Approved
0.8286	Intermediate Similarity	NPD5408	Approved
0.8286	Intermediate Similarity	NPD5405	Approved
0.8264	Intermediate Similarity	NPD7390	Discontinued
0.8082	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD943	Approved
0.7987	Intermediate Similarity	NPD3226	Approved
0.7972	Intermediate Similarity	NPD2346	Discontinued
0.7941	Intermediate Similarity	NPD1164	Approved
0.7832	Intermediate Similarity	NPD1510	Phase 2
0.7832	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7771	Intermediate Similarity	NPD6232	Discontinued
0.7736	Intermediate Similarity	NPD7473	Discontinued
0.7692	Intermediate Similarity	NPD1607	Approved
0.763	Intermediate Similarity	NPD3019	Approved
0.7603	Intermediate Similarity	NPD2344	Approved
0.7595	Intermediate Similarity	NPD6959	Discontinued
0.7584	Intermediate Similarity	NPD3300	Phase 2
0.7582	Intermediate Similarity	NPD4380	Phase 2
0.7556	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1240	Approved
0.7551	Intermediate Similarity	NPD1549	Phase 2
0.7548	Intermediate Similarity	NPD7819	Suspended
0.7535	Intermediate Similarity	NPD3764	Approved
0.7535	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD2932	Approved
0.7483	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2532	Approved
0.7483	Intermediate Similarity	NPD2533	Approved
0.7483	Intermediate Similarity	NPD2534	Approved
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2799	Discontinued
0.745	Intermediate Similarity	NPD7003	Approved
0.7442	Intermediate Similarity	NPD2342	Discontinued
0.7436	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7458	Discontinued
0.74	Intermediate Similarity	NPD2309	Approved
0.7383	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1471	Phase 3
0.7357	Intermediate Similarity	NPD1283	Approved
0.7347	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5951	Approved
0.731	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1511	Approved
0.7299	Intermediate Similarity	NPD1651	Approved
0.7278	Intermediate Similarity	NPD8150	Discontinued
0.7278	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1934	Approved
0.7255	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2798	Approved
0.7252	Intermediate Similarity	NPD9266	Approved
0.7252	Intermediate Similarity	NPD74	Approved
0.7214	Intermediate Similarity	NPD3972	Approved
0.7212	Intermediate Similarity	NPD5844	Phase 1
0.7209	Intermediate Similarity	NPD1237	Approved
0.7208	Intermediate Similarity	NPD1512	Approved
0.7206	Intermediate Similarity	NPD9493	Approved
0.7202	Intermediate Similarity	NPD8313	Approved
0.7202	Intermediate Similarity	NPD8312	Approved
0.7197	Intermediate Similarity	NPD7411	Suspended
0.7194	Intermediate Similarity	NPD3023	Approved
0.7194	Intermediate Similarity	NPD3026	Approved
0.7193	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3749	Approved
0.7176	Intermediate Similarity	NPD9267	Approved
0.7176	Intermediate Similarity	NPD9263	Approved
0.7176	Intermediate Similarity	NPD9264	Approved
0.7176	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3025	Approved
0.7174	Intermediate Similarity	NPD3024	Approved
0.7164	Intermediate Similarity	NPD7635	Approved
0.7143	Intermediate Similarity	NPD1281	Approved
0.7126	Intermediate Similarity	NPD6535	Approved
0.7126	Intermediate Similarity	NPD6534	Approved
0.7123	Intermediate Similarity	NPD6663	Approved
0.7113	Intermediate Similarity	NPD1876	Approved
0.7107	Intermediate Similarity	NPD2801	Approved
0.7105	Intermediate Similarity	NPD3750	Approved
0.7105	Intermediate Similarity	NPD4628	Phase 3
0.7105	Intermediate Similarity	NPD8166	Discontinued
0.7101	Intermediate Similarity	NPD9545	Approved
0.7101	Intermediate Similarity	NPD3091	Approved
0.7097	Intermediate Similarity	NPD6273	Approved
0.7083	Intermediate Similarity	NPD5736	Approved
0.7081	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7075	Discontinued
0.7069	Intermediate Similarity	NPD6212	Phase 3
0.7069	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6213	Phase 3
0.7067	Intermediate Similarity	NPD1551	Phase 2
0.7067	Intermediate Similarity	NPD2796	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7048	Intermediate Similarity	NPD3818	Discontinued
0.703	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6166	Phase 2
0.703	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6782	Approved
0.7022	Intermediate Similarity	NPD6781	Approved
0.7022	Intermediate Similarity	NPD6776	Approved
0.7022	Intermediate Similarity	NPD6780	Approved
0.7022	Intermediate Similarity	NPD6778	Approved
0.7022	Intermediate Similarity	NPD6777	Approved
0.7022	Intermediate Similarity	NPD6779	Approved
0.702	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3882	Suspended
0.7019	Intermediate Similarity	NPD7768	Phase 2
0.7006	Intermediate Similarity	NPD7699	Phase 2
0.7006	Intermediate Similarity	NPD7700	Phase 2
0.7	Intermediate Similarity	NPD2286	Discontinued
0.7	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5494	Approved
0.6993	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6559	Discontinued
0.6972	Remote Similarity	NPD4878	Approved
0.6972	Remote Similarity	NPD9269	Phase 2
0.6966	Remote Similarity	NPD9494	Approved
0.6959	Remote Similarity	NPD2979	Phase 3
0.6948	Remote Similarity	NPD6190	Approved
0.6944	Remote Similarity	NPD3094	Phase 2
0.6937	Remote Similarity	NPD6801	Discontinued
0.6934	Remote Similarity	NPD9281	Approved
0.6929	Remote Similarity	NPD9268	Approved
0.6928	Remote Similarity	NPD2800	Approved
0.6918	Remote Similarity	NPD6599	Discontinued
0.6914	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD230	Phase 1
0.6909	Remote Similarity	NPD5710	Approved
0.6909	Remote Similarity	NPD5711	Approved
0.6906	Remote Similarity	NPD7435	Discontinued
0.6906	Remote Similarity	NPD7697	Approved
0.6906	Remote Similarity	NPD7696	Phase 3
0.6906	Remote Similarity	NPD7698	Approved
0.6901	Remote Similarity	NPD3092	Approved
0.6889	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3400	Discontinued
0.6879	Remote Similarity	NPD3095	Discontinued
0.6879	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD288	Approved
0.6871	Remote Similarity	NPD7008	Discontinued
0.687	Remote Similarity	NPD9261	Approved
0.6868	Remote Similarity	NPD8320	Phase 1
0.6868	Remote Similarity	NPD7871	Phase 2
0.6868	Remote Similarity	NPD7870	Phase 2
0.6868	Remote Similarity	NPD8319	Approved
0.6852	Remote Similarity	NPD2296	Approved
0.6845	Remote Similarity	NPD7177	Discontinued
0.6845	Remote Similarity	NPD3751	Discontinued
0.6842	Remote Similarity	NPD36	Approved
0.6842	Remote Similarity	NPD5026	Approved
0.6842	Remote Similarity	NPD5028	Approved
0.6842	Remote Similarity	NPD5034	Approved
0.6842	Remote Similarity	NPD4955	Approved
0.6842	Remote Similarity	NPD4954	Approved
0.6838	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD920	Approved
0.6832	Remote Similarity	NPD6844	Discontinued
0.6824	Remote Similarity	NPD411	Approved
0.6815	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD497	Approved
0.6809	Remote Similarity	NPD5691	Approved
0.6806	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6020	Phase 2
0.6805	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.68	Remote Similarity	NPD447	Suspended
0.68	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD844	Approved
0.6794	Remote Similarity	NPD1932	Approved
0.679	Remote Similarity	NPD1465	Phase 2
0.6784	Remote Similarity	NPD5030	Phase 2
0.6779	Remote Similarity	NPD520	Approved
0.6776	Remote Similarity	NPD4308	Phase 3
0.6776	Remote Similarity	NPD3748	Approved
0.6769	Remote Similarity	NPD3020	Approved
0.6765	Remote Similarity	NPD7074	Phase 3
0.6763	Remote Similarity	NPD3317	Approved
0.6757	Remote Similarity	NPD7701	Phase 2
0.6752	Remote Similarity	NPD6799	Approved
0.6748	Remote Similarity	NPD5402	Approved
0.6748	Remote Similarity	NPD3817	Phase 2
0.6748	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1930	Approved
0.6742	Remote Similarity	NPD1929	Approved
0.6742	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD498	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