NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.08
Volume:	250.242
LogP:	4.284
LogD:	3.13
LogS:	-3.443
# Rotatable Bonds:	0
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.528
Synthetic Accessibility Score:	2.368
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.988
MDCK Permeability:	1.1415655535529368e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.758
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	98.82621002197266%
Volume Distribution (VD):	0.565
Pgp-substrate:	2.0161948204040527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.692
CYP2C19-inhibitor:	0.392
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.683
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.746
CYP2D6-substrate:	0.57
CYP3A4-inhibitor:	0.179
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	9.19
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.032
Drug-inuced Liver Injury (DILI):	0.767
AMES Toxicity:	0.761
Rat Oral Acute Toxicity:	0.555
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.954
Carcinogencity:	0.716
Eye Corrosion:	0.057
Eye Irritation:	0.965
Respiratory Toxicity:	0.771

Download Data

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

Natural Product: NPC173978

Natural Product ID:	NPC173978
*Common Name:**	1,8-Dihydroxy-3-Methyl-10H-Anthracen-9-One
IUPAC Name:	1,8-dihydroxy-3-methyl-10H-anthracen-9-one
Synonyms:
Standard InCHIKey:	ZZBWSNKBZKPGAK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O3/c1-8-5-10-7-9-3-2-4-11(16)13(9)15(18)14(10)12(17)6-8/h2-6,16-17H,7H2,1H3
SMILES:	Cc1cc2Cc3cccc(c3C(=O)c2c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL122196
PubChem CID:	68111
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087602]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[12932124]
NPO8921	Senna obtusifolia	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[2213033]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29517220]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3417561]
NPO3980	Frangula purshiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19050	Garcinia polyantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8921	Senna obtusifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27140	Amanita phalloides	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8921	Senna obtusifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10239	Magnolia figo	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8921	Senna obtusifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27140	Amanita phalloides	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24629	Achromobacter denitrificans	Species	Alcaligenaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3980	Frangula purshiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27790	Delia arenicola	Species	Anthomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19050	Garcinia polyantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27454	Turbo cornutus	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4132	Cranfillia fluviatilis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26972	Baccharis potosina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27873	Ravenia spectabilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17822	Fridericia triplinervia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27564	Stevia berlandieri	Species	Asteraceae	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	2
Others	7

Activity Type	# Activity
Cell Line	2
Individual Protein	1
NON-MOLECULAR	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3021	Individual Protein	Arachidonate 5-lipoxygenase	Bos taurus	IC50	>	30000.0	nM	PMID[452401]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	=	1500.0	nM	PMID[452401]
NPT941	Cell Line	HaCaT	Homo sapiens	LDH	=	211.0	MU	PMID[452401]
NPT35	Others	n.a.		LogP	=	4.8	n.a.	PMID[452401]
NPT610	Others	Molecular identity unknown		kDPPH	=	15.3	M-1 s-1	PMID[452401]
NPT610	Others	Molecular identity unknown		Ratio	=	2.35	n.a.	PMID[452401]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	>	0.25	mg/ml	PMID[452402]

☑ 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 NPC173978 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	365
0.1-0.2	1710
0.2-0.3	3683
0.3-0.4	11254
0.4-0.5	7874
0.5-0.6	6163
0.6-0.7	7718
0.7-0.8	3418
0.8-0.85	352
0.85-0.9	122
0.9-0.95	36
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC282923
0.95	High Similarity	NPC142956
0.9435	High Similarity	NPC72669
0.9435	High Similarity	NPC205992
0.9435	High Similarity	NPC474517
0.9431	High Similarity	NPC99731
0.9421	High Similarity	NPC103540
0.935	High Similarity	NPC48248
0.9333	High Similarity	NPC300274
0.9286	High Similarity	NPC115458
0.9256	High Similarity	NPC375356
0.9213	High Similarity	NPC161964
0.9213	High Similarity	NPC472262
0.9213	High Similarity	NPC287604
0.9206	High Similarity	NPC70622
0.9187	High Similarity	NPC3224
0.9187	High Similarity	NPC160499
0.9174	High Similarity	NPC307174
0.9141	High Similarity	NPC283088
0.9134	High Similarity	NPC314048
0.9134	High Similarity	NPC267205
0.912	High Similarity	NPC34414
0.912	High Similarity	NPC146647
0.907	High Similarity	NPC474813
0.907	High Similarity	NPC272268
0.9062	High Similarity	NPC288089
0.9055	High Similarity	NPC58685
0.9048	High Similarity	NPC136588
0.9048	High Similarity	NPC199253
0.9032	High Similarity	NPC96915
0.9024	High Similarity	NPC152525
0.9024	High Similarity	NPC68756
0.9	High Similarity	NPC53414
0.9	High Similarity	NPC53206
0.9	High Similarity	NPC245923
0.8984	High Similarity	NPC225051
0.8931	High Similarity	NPC416
0.8931	High Similarity	NPC13715
0.8931	High Similarity	NPC61398
0.8926	High Similarity	NPC285829
0.8926	High Similarity	NPC206778
0.8923	High Similarity	NPC191976
0.8923	High Similarity	NPC254847
0.8915	High Similarity	NPC12070
0.8908	High Similarity	NPC477453
0.8898	High Similarity	NPC55949
0.8898	High Similarity	NPC31799
0.888	High Similarity	NPC231774
0.8871	High Similarity	NPC234890
0.8871	High Similarity	NPC236189
0.8871	High Similarity	NPC74507
0.8864	High Similarity	NPC26924
0.8864	High Similarity	NPC138099
0.8864	High Similarity	NPC1268
0.8864	High Similarity	NPC242994
0.8855	High Similarity	NPC471905
0.8855	High Similarity	NPC305060
0.8846	High Similarity	NPC249272
0.8846	High Similarity	NPC80035
0.8846	High Similarity	NPC161632
0.8837	High Similarity	NPC114183
0.8837	High Similarity	NPC52407
0.8837	High Similarity	NPC53896
0.8828	High Similarity	NPC41847
0.8828	High Similarity	NPC244699
0.8824	High Similarity	NPC161304
0.8819	High Similarity	NPC278928
0.8819	High Similarity	NPC276238
0.8797	High Similarity	NPC169452
0.8797	High Similarity	NPC315578
0.8797	High Similarity	NPC181560
0.8779	High Similarity	NPC155211
0.8779	High Similarity	NPC141934
0.8769	High Similarity	NPC270899
0.8769	High Similarity	NPC44437
0.8769	High Similarity	NPC50924
0.875	High Similarity	NPC475741
0.874	High Similarity	NPC96024
0.8731	High Similarity	NPC124365
0.8722	High Similarity	NPC143438
0.872	High Similarity	NPC199273
0.8712	High Similarity	NPC53001
0.871	High Similarity	NPC176208
0.8702	High Similarity	NPC258502
0.8682	High Similarity	NPC85342
0.8672	High Similarity	NPC92624
0.8667	High Similarity	NPC239136
0.8667	High Similarity	NPC193555
0.8667	High Similarity	NPC19631
0.8661	High Similarity	NPC176130
0.8661	High Similarity	NPC78364
0.8661	High Similarity	NPC471530
0.8661	High Similarity	NPC84672
0.8661	High Similarity	NPC69424
0.8657	High Similarity	NPC96421
0.8657	High Similarity	NPC225243
0.8647	High Similarity	NPC87723
0.8647	High Similarity	NPC4214
0.8636	High Similarity	NPC118919
0.8629	High Similarity	NPC120545
0.8626	High Similarity	NPC282780
0.8626	High Similarity	NPC166480
0.8618	High Similarity	NPC473662
0.8618	High Similarity	NPC7151
0.8618	High Similarity	NPC216297
0.8615	High Similarity	NPC309430
0.8607	High Similarity	NPC41567
0.8605	High Similarity	NPC259942
0.8605	High Similarity	NPC31539
0.8603	High Similarity	NPC313047
0.8603	High Similarity	NPC471682
0.8603	High Similarity	NPC474203
0.8603	High Similarity	NPC296752
0.8603	High Similarity	NPC295712
0.8603	High Similarity	NPC451542
0.8595	High Similarity	NPC108288
0.8593	High Similarity	NPC246638
0.8593	High Similarity	NPC305845
0.8593	High Similarity	NPC204045
0.8583	High Similarity	NPC1991
0.8583	High Similarity	NPC49647
0.8583	High Similarity	NPC295202
0.8583	High Similarity	NPC306765
0.8583	High Similarity	NPC227741
0.8583	High Similarity	NPC254492
0.8583	High Similarity	NPC136342
0.8582	High Similarity	NPC190457
0.8571	High Similarity	NPC62272
0.8571	High Similarity	NPC310540
0.856	High Similarity	NPC244351
0.856	High Similarity	NPC282577
0.856	High Similarity	NPC283514
0.856	High Similarity	NPC91478
0.855	High Similarity	NPC294226
0.854	High Similarity	NPC193703
0.854	High Similarity	NPC21599
0.854	High Similarity	NPC10764
0.8538	High Similarity	NPC93015
0.8538	High Similarity	NPC17083
0.8529	High Similarity	NPC474961
0.8529	High Similarity	NPC73061
0.8529	High Similarity	NPC135524
0.8529	High Similarity	NPC257644
0.8527	High Similarity	NPC109123
0.8525	High Similarity	NPC125252
0.8516	High Similarity	NPC72667
0.8504	High Similarity	NPC131799
0.8496	Intermediate Similarity	NPC472308
0.8496	Intermediate Similarity	NPC315275
0.8496	Intermediate Similarity	NPC193358
0.8492	Intermediate Similarity	NPC275145
0.8485	Intermediate Similarity	NPC1249
0.848	Intermediate Similarity	NPC198336
0.848	Intermediate Similarity	NPC154696
0.8478	Intermediate Similarity	NPC170055
0.8478	Intermediate Similarity	NPC471683
0.8473	Intermediate Similarity	NPC110609
0.8473	Intermediate Similarity	NPC175738
0.8473	Intermediate Similarity	NPC242358
0.8473	Intermediate Similarity	NPC246693
0.8467	Intermediate Similarity	NPC293545
0.8467	Intermediate Similarity	NPC174905
0.8462	Intermediate Similarity	NPC198305
0.8462	Intermediate Similarity	NPC62219
0.8462	Intermediate Similarity	NPC108129
0.8456	Intermediate Similarity	NPC110810
0.8456	Intermediate Similarity	NPC290550
0.8456	Intermediate Similarity	NPC106519
0.8456	Intermediate Similarity	NPC477275
0.8456	Intermediate Similarity	NPC187843
0.8456	Intermediate Similarity	NPC91019
0.8433	Intermediate Similarity	NPC147418
0.8425	Intermediate Similarity	NPC164014
0.8417	Intermediate Similarity	NPC285122
0.8417	Intermediate Similarity	NPC300540
0.8409	Intermediate Similarity	NPC48036
0.8409	Intermediate Similarity	NPC254603
0.8406	Intermediate Similarity	NPC84568
0.8406	Intermediate Similarity	NPC471906
0.8406	Intermediate Similarity	NPC48762
0.8406	Intermediate Similarity	NPC48130
0.8406	Intermediate Similarity	NPC300684
0.8406	Intermediate Similarity	NPC227841
0.8406	Intermediate Similarity	NPC218866
0.8406	Intermediate Similarity	NPC244691
0.84	Intermediate Similarity	NPC259703
0.84	Intermediate Similarity	NPC178395
0.84	Intermediate Similarity	NPC244994
0.84	Intermediate Similarity	NPC472046
0.84	Intermediate Similarity	NPC301987
0.84	Intermediate Similarity	NPC190971
0.84	Intermediate Similarity	NPC115188
0.84	Intermediate Similarity	NPC35856
0.84	Intermediate Similarity	NPC179092
0.84	Intermediate Similarity	NPC222876
0.84	Intermediate Similarity	NPC26433
0.84	Intermediate Similarity	NPC272454
0.84	Intermediate Similarity	NPC292665
0.84	Intermediate Similarity	NPC159760
0.84	Intermediate Similarity	NPC32322

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 NPC173978 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	970
0.2-0.3	1236
0.3-0.4	2694
0.4-0.5	2167
0.5-0.6	1190
0.6-0.7	423
0.7-0.8	96
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9744	High Similarity	NPD1201	Approved
0.9421	High Similarity	NPD1470	Approved
0.8923	High Similarity	NPD1509	Clinical (unspecified phase)
0.8595	High Similarity	NPD405	Clinical (unspecified phase)
0.8571	High Similarity	NPD5406	Approved
0.8571	High Similarity	NPD5408	Approved
0.8571	High Similarity	NPD5405	Approved
0.8571	High Similarity	NPD5404	Approved
0.8406	Intermediate Similarity	NPD7390	Discontinued
0.8112	Intermediate Similarity	NPD3226	Approved
0.8102	Intermediate Similarity	NPD2346	Discontinued
0.8085	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1164	Approved
0.8031	Intermediate Similarity	NPD3019	Approved
0.8	Intermediate Similarity	NPD2342	Discontinued
0.7926	Intermediate Similarity	NPD943	Approved
0.7891	Intermediate Similarity	NPD2932	Approved
0.784	Intermediate Similarity	NPD5951	Approved
0.7817	Intermediate Similarity	NPD3300	Phase 2
0.781	Intermediate Similarity	NPD1607	Approved
0.7744	Intermediate Similarity	NPD2798	Approved
0.768	Intermediate Similarity	NPD7635	Approved
0.7664	Intermediate Similarity	NPD1240	Approved
0.7647	Intermediate Similarity	NPD3764	Approved
0.7643	Intermediate Similarity	NPD2935	Discontinued
0.7642	Intermediate Similarity	NPD74	Approved
0.7642	Intermediate Similarity	NPD9266	Approved
0.7594	Intermediate Similarity	NPD1283	Approved
0.7578	Intermediate Similarity	NPD9493	Approved
0.7571	Intermediate Similarity	NPD1510	Phase 2
0.7571	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD9264	Approved
0.7561	Intermediate Similarity	NPD9267	Approved
0.7561	Intermediate Similarity	NPD9263	Approved
0.7552	Intermediate Similarity	NPD7003	Approved
0.7542	Intermediate Similarity	NPD288	Approved
0.7538	Intermediate Similarity	NPD1651	Approved
0.7538	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6232	Discontinued
0.7518	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7473	Discontinued
0.7481	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6959	Discontinued
0.7466	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD844	Approved
0.7447	Intermediate Similarity	NPD2799	Discontinued
0.7447	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD3023	Approved
0.7424	Intermediate Similarity	NPD3026	Approved
0.7417	Intermediate Similarity	NPD7819	Suspended
0.7413	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3024	Approved
0.7405	Intermediate Similarity	NPD3025	Approved
0.7368	Intermediate Similarity	NPD1281	Approved
0.7368	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2344	Approved
0.7343	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3750	Approved
0.7303	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4750	Phase 3
0.7292	Intermediate Similarity	NPD1549	Phase 2
0.728	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1203	Approved
0.7279	Intermediate Similarity	NPD1511	Approved
0.7273	Intermediate Similarity	NPD1551	Phase 2
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1930	Approved
0.7236	Intermediate Similarity	NPD1929	Approved
0.7236	Intermediate Similarity	NPD9261	Approved
0.7236	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2534	Approved
0.723	Intermediate Similarity	NPD2533	Approved
0.723	Intermediate Similarity	NPD2532	Approved
0.7218	Intermediate Similarity	NPD2286	Discontinued
0.7218	Intermediate Similarity	NPD4626	Approved
0.7214	Intermediate Similarity	NPD6663	Approved
0.7213	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4625	Phase 3
0.7185	Intermediate Similarity	NPD1608	Approved
0.7181	Intermediate Similarity	NPD1512	Approved
0.7177	Intermediate Similarity	NPD1237	Approved
0.7174	Intermediate Similarity	NPD5736	Approved
0.7154	Intermediate Similarity	NPD9281	Approved
0.7154	Intermediate Similarity	NPD497	Approved
0.7153	Intermediate Similarity	NPD6100	Approved
0.7153	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD845	Approved
0.7143	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD411	Approved
0.7131	Intermediate Similarity	NPD3020	Approved
0.7124	Intermediate Similarity	NPD1934	Approved
0.7105	Intermediate Similarity	NPD4380	Phase 2
0.7103	Intermediate Similarity	NPD1471	Phase 3
0.7097	Intermediate Similarity	NPD7768	Phase 2
0.7083	Intermediate Similarity	NPD4308	Phase 3
0.708	Intermediate Similarity	NPD1876	Approved
0.7077	Intermediate Similarity	NPD498	Approved
0.7077	Intermediate Similarity	NPD495	Approved
0.7077	Intermediate Similarity	NPD496	Approved
0.7073	Intermediate Similarity	NPD8312	Approved
0.7073	Intermediate Similarity	NPD8313	Approved
0.7071	Intermediate Similarity	NPD7008	Discontinued
0.7071	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3091	Approved
0.7068	Intermediate Similarity	NPD9545	Approved
0.7059	Intermediate Similarity	NPD9717	Approved
0.7059	Intermediate Similarity	NPD7411	Suspended
0.7059	Intermediate Similarity	NPD4878	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7051	Intermediate Similarity	NPD3749	Approved
0.7048	Intermediate Similarity	NPD8150	Discontinued
0.7039	Intermediate Similarity	NPD7458	Discontinued
0.7034	Intermediate Similarity	NPD2796	Approved
0.7029	Intermediate Similarity	NPD2797	Approved
0.7025	Intermediate Similarity	NPD2859	Approved
0.7025	Intermediate Similarity	NPD2860	Approved
0.7007	Intermediate Similarity	NPD1755	Approved
0.6985	Remote Similarity	NPD3092	Approved
0.6975	Remote Similarity	NPD6020	Phase 2
0.6968	Remote Similarity	NPD2801	Approved
0.6966	Remote Similarity	NPD3748	Approved
0.6964	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4059	Approved
0.6963	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD17	Approved
0.6959	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8166	Discontinued
0.6954	Remote Similarity	NPD6273	Approved
0.6953	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7075	Discontinued
0.6942	Remote Similarity	NPD2934	Approved
0.6942	Remote Similarity	NPD2933	Approved
0.6942	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1242	Phase 1
0.6923	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7177	Discontinued
0.6901	Remote Similarity	NPD3268	Approved
0.6899	Remote Similarity	NPD3021	Approved
0.6899	Remote Similarity	NPD3022	Approved
0.6894	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2800	Approved
0.6889	Remote Similarity	NPD4093	Discontinued
0.6889	Remote Similarity	NPD5691	Approved
0.6885	Remote Similarity	NPD1809	Phase 2
0.6884	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.688	Remote Similarity	NPD940	Approved
0.688	Remote Similarity	NPD1932	Approved
0.688	Remote Similarity	NPD846	Approved
0.6875	Remote Similarity	NPD447	Suspended
0.6871	Remote Similarity	NPD5844	Phase 1
0.6871	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD1611	Approved
0.6859	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2066	Phase 3
0.6848	Remote Similarity	NPD6559	Discontinued
0.6848	Remote Similarity	NPD5029	Approved
0.6848	Remote Similarity	NPD5027	Approved
0.6848	Remote Similarity	NPD5031	Approved
0.6846	Remote Similarity	NPD4628	Phase 3
0.6846	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4307	Phase 2
0.6806	Remote Similarity	NPD2979	Phase 3
0.6803	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6166	Phase 2
0.6786	Remote Similarity	NPD3094	Phase 2
0.6786	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1243	Approved
0.6776	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6599	Discontinued
0.6772	Remote Similarity	NPD3882	Suspended
0.6769	Remote Similarity	NPD1792	Phase 2
0.6761	Remote Similarity	NPD6832	Phase 2
0.6759	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7610	Discontinued
0.6736	Remote Similarity	NPD520	Approved
0.6736	Remote Similarity	NPD8032	Phase 2
0.6733	Remote Similarity	NPD3400	Discontinued
0.6715	Remote Similarity	NPD3095	Discontinued
0.6714	Remote Similarity	NPD6696	Suspended
0.6712	Remote Similarity	NPD6651	Approved
0.6709	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD36	Approved
0.6707	Remote Similarity	NPD5034	Approved
0.6707	Remote Similarity	NPD5028	Approved
0.6707	Remote Similarity	NPD4955	Approved
0.6707	Remote Similarity	NPD4954	Approved
0.6707	Remote Similarity	NPD5026	Approved
0.6705	Remote Similarity	NPD6534	Approved
0.6705	Remote Similarity	NPD6535	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