NPASS Compound

Structure

NPC48248 OpenBabel07101718302D 24 26 0 0 0 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 9 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 13 1 0 0 0 0 6 10 1 0 0 0 0 7 14 2 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 15 2 0 0 0 0 11 13 1 0 0 0 0 12 16 2 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 23 2 0 0 0 0 19 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.1
Volume:	331.734
LogP:	4.329
LogD:	2.574
LogS:	-3.624
# Rotatable Bonds:	2
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.248
Synthetic Accessibility Score:	2.878
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.135
MDCK Permeability:	1.0254710105073173e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.095
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	97.92215728759766%
Volume Distribution (VD):	0.423
Pgp-substrate:	5.172298908233643%

ADMET: Metabolism

CYP1A2-inhibitor:	0.941
CYP1A2-substrate:	0.608
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.692
CYP2C9-substrate:	0.631
CYP2D6-inhibitor:	0.549
CYP2D6-substrate:	0.269
CYP3A4-inhibitor:	0.139
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	5.291
Half-life (T1/2):	0.755

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.765
Rat Oral Acute Toxicity:	0.359
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.951
Carcinogencity:	0.731
Eye Corrosion:	0.01
Eye Irritation:	0.947
Respiratory Toxicity:	0.764

Download Data

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

Natural Product: NPC48248

Natural Product ID:	NPC48248
*Common Name:**	3-Butyryl-1,8-Dihydroxy-2-Methylphenanthrene-9,10-Dione
IUPAC Name:	3-butanoyl-1,8-dihydroxy-2-methylphenanthrene-9,10-dione
Synonyms:	SCH-68631
Standard InCHIKey:	YJQYHFMKGAVKDP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O5/c1-3-5-13(20)11-8-12-10-6-4-7-14(21)15(10)18(23)19(24)16(12)17(22)9(11)2/h4,6-8,21-22H,3,5H2,1-2H3
SMILES:	CCCC(=O)c1cc2c(c(c1C)O)C(=O)C(=O)c1c2cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL179197
PubChem CID:	482190
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0002571] Phenanthraquinones

*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
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170686]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16156520]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21043476]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	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	4

Activity Type	# Activity
Individual Protein	2
Others	1
PROTEIN COMPLEX	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5224	Individual Protein	NS3	Hepatitis C virus	IC50	=	7000.0	nM	PMID[536265]
NPT1869	Individual Protein	Catenin beta-1	Homo sapiens	IC50	<	10000.0	nM	PMID[536267]
NPT2	Others	Unspecified		IC50	=	7700.0	nM	PMID[536266]
NPT26688	PROTEIN COMPLEX	TCF4-CTNNB1 complex	Homo sapiens	IC50	=	2400.0	nM	PMID[536268]

☑ 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 NPC48248 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	327
0.1-0.2	1608
0.2-0.3	3546
0.3-0.4	10392
0.4-0.5	8731
0.5-0.6	6079
0.6-0.7	7924
0.7-0.8	3518
0.8-0.85	362
0.85-0.9	150
0.9-0.95	51
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9516	High Similarity	NPC282923
0.9508	High Similarity	NPC142956
0.9453	High Similarity	NPC283088
0.9449	High Similarity	NPC115458
0.9449	High Similarity	NPC225051
0.944	High Similarity	NPC146647
0.944	High Similarity	NPC34414
0.9426	High Similarity	NPC375356
0.9365	High Similarity	NPC55949
0.935	High Similarity	NPC173978
0.9344	High Similarity	NPC300274
0.9308	High Similarity	NPC245923
0.9291	High Similarity	NPC205992
0.9291	High Similarity	NPC244699
0.9286	High Similarity	NPC99731
0.9274	High Similarity	NPC103540
0.9231	High Similarity	NPC272268
0.9231	High Similarity	NPC474813
0.9231	High Similarity	NPC155211
0.9225	High Similarity	NPC50924
0.9219	High Similarity	NPC58685
0.9213	High Similarity	NPC199253
0.9213	High Similarity	NPC136588
0.92	High Similarity	NPC96915
0.9187	High Similarity	NPC307174
0.9154	High Similarity	NPC80035
0.9147	High Similarity	NPC53896
0.9141	High Similarity	NPC72669
0.9141	High Similarity	NPC474517
0.9077	High Similarity	NPC287604
0.9077	High Similarity	NPC161964
0.9077	High Similarity	NPC472262
0.907	High Similarity	NPC70622
0.9062	High Similarity	NPC31799
0.9055	High Similarity	NPC96024
0.9048	High Similarity	NPC3224
0.9048	High Similarity	NPC306765
0.9048	High Similarity	NPC160499
0.9023	High Similarity	NPC138099
0.9023	High Similarity	NPC242994
0.9	High Similarity	NPC314048
0.9	High Similarity	NPC52407
0.8984	High Similarity	NPC276238
0.8976	High Similarity	NPC471530
0.8963	High Similarity	NPC239136
0.8963	High Similarity	NPC19631
0.8955	High Similarity	NPC315578
0.8955	High Similarity	NPC181560
0.8955	High Similarity	NPC169452
0.8947	High Similarity	NPC13715
0.8947	High Similarity	NPC4214
0.8943	High Similarity	NPC206778
0.8943	High Similarity	NPC285829
0.8931	High Similarity	NPC288089
0.8931	High Similarity	NPC12070
0.8926	High Similarity	NPC477453
0.8915	High Similarity	NPC31539
0.8889	High Similarity	NPC68756
0.8889	High Similarity	NPC152525
0.8889	High Similarity	NPC236189
0.8881	High Similarity	NPC1268
0.8881	High Similarity	NPC26924
0.888	High Similarity	NPC176208
0.8872	High Similarity	NPC471905
0.8872	High Similarity	NPC53206
0.8872	High Similarity	NPC53414
0.8864	High Similarity	NPC249272
0.8864	High Similarity	NPC258502
0.8855	High Similarity	NPC114183
0.8846	High Similarity	NPC85342
0.8843	High Similarity	NPC161304
0.8828	High Similarity	NPC84672
0.8828	High Similarity	NPC69424
0.8828	High Similarity	NPC78364
0.8828	High Similarity	NPC176130
0.8824	High Similarity	NPC193555
0.8824	High Similarity	NPC69755
0.8815	High Similarity	NPC225243
0.8815	High Similarity	NPC96421
0.881	High Similarity	NPC275145
0.8806	High Similarity	NPC416
0.8806	High Similarity	NPC61398
0.8797	High Similarity	NPC193358
0.8797	High Similarity	NPC191976
0.8797	High Similarity	NPC472308
0.8797	High Similarity	NPC254847
0.8788	High Similarity	NPC270899
0.8788	High Similarity	NPC282780
0.8788	High Similarity	NPC166480
0.8769	High Similarity	NPC108129
0.8759	High Similarity	NPC471682
0.875	High Similarity	NPC231774
0.875	High Similarity	NPC246638
0.875	High Similarity	NPC49647
0.875	High Similarity	NPC136342
0.875	High Similarity	NPC295202
0.875	High Similarity	NPC254492
0.875	High Similarity	NPC227741
0.875	High Similarity	NPC124365
0.874	High Similarity	NPC199273
0.874	High Similarity	NPC234890
0.874	High Similarity	NPC310540
0.874	High Similarity	NPC74507
0.8731	High Similarity	NPC53001
0.8731	High Similarity	NPC62272
0.8731	High Similarity	NPC305060
0.873	High Similarity	NPC91478
0.8722	High Similarity	NPC161632
0.8712	High Similarity	NPC294226
0.8712	High Similarity	NPC267205
0.8702	High Similarity	NPC93015
0.8702	High Similarity	NPC17083
0.8696	High Similarity	NPC10764
0.8686	High Similarity	NPC135524
0.8686	High Similarity	NPC257644
0.8682	High Similarity	NPC72667
0.8672	High Similarity	NPC131799
0.8667	High Similarity	NPC87723
0.8657	High Similarity	NPC141934
0.8651	High Similarity	NPC120545
0.8647	High Similarity	NPC44437
0.8647	High Similarity	NPC202225
0.8636	High Similarity	NPC246693
0.8636	High Similarity	NPC110609
0.8636	High Similarity	NPC242358
0.8633	High Similarity	NPC471683
0.8626	High Similarity	NPC198305
0.8623	High Similarity	NPC66593
0.8623	High Similarity	NPC296752
0.8618	High Similarity	NPC108288
0.8613	High Similarity	NPC204045
0.8613	High Similarity	NPC305845
0.8603	High Similarity	NPC143438
0.8594	High Similarity	NPC164014
0.8583	High Similarity	NPC244351
0.8583	High Similarity	NPC282577
0.8582	High Similarity	NPC153088
0.8561	High Similarity	NPC41847
0.8561	High Similarity	NPC193703
0.8561	High Similarity	NPC471851
0.8561	High Similarity	NPC21599
0.8561	High Similarity	NPC79627
0.8551	High Similarity	NPC474961
0.855	High Similarity	NPC25736
0.855	High Similarity	NPC278928
0.855	High Similarity	NPC171460
0.855	High Similarity	NPC57552
0.855	High Similarity	NPC109123
0.855	High Similarity	NPC303910
0.8548	High Similarity	NPC269414
0.8529	High Similarity	NPC206207
0.8519	High Similarity	NPC474311
0.8519	High Similarity	NPC118919
0.8511	High Similarity	NPC37709
0.8507	High Similarity	NPC1249
0.8504	High Similarity	NPC154696
0.85	High Similarity	NPC478019
0.85	High Similarity	NPC34482
0.8496	Intermediate Similarity	NPC309430
0.8492	Intermediate Similarity	NPC473662
0.8492	Intermediate Similarity	NPC216297
0.8492	Intermediate Similarity	NPC7151
0.8489	Intermediate Similarity	NPC313047
0.8489	Intermediate Similarity	NPC53016
0.8489	Intermediate Similarity	NPC474203
0.8489	Intermediate Similarity	NPC451542
0.8489	Intermediate Similarity	NPC295712
0.8485	Intermediate Similarity	NPC475741
0.8485	Intermediate Similarity	NPC27659
0.848	Intermediate Similarity	NPC41567
0.8478	Intermediate Similarity	NPC477275
0.8478	Intermediate Similarity	NPC187843
0.8473	Intermediate Similarity	NPC237225
0.8467	Intermediate Similarity	NPC190457
0.8462	Intermediate Similarity	NPC71610
0.8462	Intermediate Similarity	NPC205766
0.8456	Intermediate Similarity	NPC475957
0.8444	Intermediate Similarity	NPC22222
0.8444	Intermediate Similarity	NPC281513
0.844	Intermediate Similarity	NPC470570
0.844	Intermediate Similarity	NPC143685
0.844	Intermediate Similarity	NPC285122
0.844	Intermediate Similarity	NPC314437
0.844	Intermediate Similarity	NPC147250
0.844	Intermediate Similarity	NPC300540
0.8438	Intermediate Similarity	NPC283514
0.8433	Intermediate Similarity	NPC111845
0.8433	Intermediate Similarity	NPC477139
0.8433	Intermediate Similarity	NPC171968
0.8433	Intermediate Similarity	NPC78307
0.8429	Intermediate Similarity	NPC244691
0.8429	Intermediate Similarity	NPC471906
0.8429	Intermediate Similarity	NPC48762
0.8429	Intermediate Similarity	NPC227841
0.8425	Intermediate Similarity	NPC35856
0.8425	Intermediate Similarity	NPC259703
0.8425	Intermediate Similarity	NPC222876
0.8425	Intermediate Similarity	NPC301987
0.8425	Intermediate Similarity	NPC292665
0.8425	Intermediate Similarity	NPC179092

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 NPC48248 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	969
0.2-0.3	1200
0.3-0.4	2557
0.4-0.5	2302
0.5-0.6	1223
0.6-0.7	465
0.7-0.8	106
0.8-0.85	6
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9274	High Similarity	NPD1470	Approved
0.9106	High Similarity	NPD1201	Approved
0.8797	High Similarity	NPD1509	Clinical (unspecified phase)
0.8731	High Similarity	NPD5405	Approved
0.8731	High Similarity	NPD5404	Approved
0.8731	High Similarity	NPD5406	Approved
0.8731	High Similarity	NPD5408	Approved
0.8618	High Similarity	NPD405	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD7390	Discontinued
0.8394	Intermediate Similarity	NPD2346	Discontinued
0.8239	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD3226	Approved
0.8106	Intermediate Similarity	NPD1164	Approved
0.8062	Intermediate Similarity	NPD3019	Approved
0.8033	Intermediate Similarity	NPD2342	Discontinued
0.8016	Intermediate Similarity	NPD5951	Approved
0.7929	Intermediate Similarity	NPD2935	Discontinued
0.7923	Intermediate Similarity	NPD2932	Approved
0.791	Intermediate Similarity	NPD2798	Approved
0.7857	Intermediate Similarity	NPD2799	Discontinued
0.7857	Intermediate Similarity	NPD7635	Approved
0.7847	Intermediate Similarity	NPD3300	Phase 2
0.7832	Intermediate Similarity	NPD7003	Approved
0.7826	Intermediate Similarity	NPD943	Approved
0.781	Intermediate Similarity	NPD2313	Discontinued
0.773	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD3764	Approved
0.7677	Intermediate Similarity	NPD6232	Discontinued
0.7652	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7473	Discontinued
0.7622	Intermediate Similarity	NPD2344	Approved
0.7594	Intermediate Similarity	NPD3023	Approved
0.7594	Intermediate Similarity	NPD3026	Approved
0.7576	Intermediate Similarity	NPD1651	Approved
0.7576	Intermediate Similarity	NPD3024	Approved
0.7576	Intermediate Similarity	NPD3025	Approved
0.754	Intermediate Similarity	NPD9266	Approved
0.754	Intermediate Similarity	NPD74	Approved
0.75	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD1283	Approved
0.7483	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD9493	Approved
0.7465	Intermediate Similarity	NPD1607	Approved
0.746	Intermediate Similarity	NPD9264	Approved
0.746	Intermediate Similarity	NPD9263	Approved
0.746	Intermediate Similarity	NPD9267	Approved
0.7451	Intermediate Similarity	NPD7819	Suspended
0.7415	Intermediate Similarity	NPD2309	Approved
0.7383	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1510	Phase 2
0.7357	Intermediate Similarity	NPD7008	Discontinued
0.7357	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD844	Approved
0.7353	Intermediate Similarity	NPD4878	Approved
0.7324	Intermediate Similarity	NPD1240	Approved
0.7319	Intermediate Similarity	NPD1203	Approved
0.7303	Intermediate Similarity	NPD7458	Discontinued
0.7295	Intermediate Similarity	NPD288	Approved
0.728	Intermediate Similarity	NPD1929	Approved
0.728	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD1930	Approved
0.7279	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1281	Approved
0.7279	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7266	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1471	Phase 3
0.7259	Intermediate Similarity	NPD2286	Discontinued
0.7259	Intermediate Similarity	NPD4626	Approved
0.7254	Intermediate Similarity	NPD6663	Approved
0.7244	Intermediate Similarity	NPD7768	Phase 2
0.7241	Intermediate Similarity	NPD4308	Phase 3
0.723	Intermediate Similarity	NPD3750	Approved
0.723	Intermediate Similarity	NPD8166	Discontinued
0.7226	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3972	Approved
0.7214	Intermediate Similarity	NPD5736	Approved
0.7212	Intermediate Similarity	NPD8312	Approved
0.7212	Intermediate Similarity	NPD8313	Approved
0.7202	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1932	Approved
0.7197	Intermediate Similarity	NPD3749	Approved
0.7197	Intermediate Similarity	NPD497	Approved
0.7197	Intermediate Similarity	NPD9281	Approved
0.7186	Intermediate Similarity	NPD8150	Discontinued
0.7183	Intermediate Similarity	NPD411	Approved
0.7179	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3020	Approved
0.7154	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9261	Approved
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1876	Approved
0.7121	Intermediate Similarity	NPD496	Approved
0.7121	Intermediate Similarity	NPD498	Approved
0.7121	Intermediate Similarity	NPD495	Approved
0.7113	Intermediate Similarity	NPD4625	Phase 3
0.7111	Intermediate Similarity	NPD3091	Approved
0.7105	Intermediate Similarity	NPD6273	Approved
0.7101	Intermediate Similarity	NPD9717	Approved
0.7097	Intermediate Similarity	NPD7411	Suspended
0.7095	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1549	Phase 2
0.709	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1237	Approved
0.7083	Intermediate Similarity	NPD2979	Phase 3
0.7077	Intermediate Similarity	NPD3022	Approved
0.7077	Intermediate Similarity	NPD4750	Phase 3
0.7077	Intermediate Similarity	NPD3021	Approved
0.7075	Intermediate Similarity	NPD1551	Phase 2
0.7073	Intermediate Similarity	NPD2860	Approved
0.7073	Intermediate Similarity	NPD2859	Approved
0.7071	Intermediate Similarity	NPD2797	Approved
0.707	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3268	Approved
0.7055	Intermediate Similarity	NPD7177	Discontinued
0.705	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD845	Approved
0.7042	Intermediate Similarity	NPD6832	Phase 2
0.704	Intermediate Similarity	NPD2066	Phase 3
0.7037	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD447	Suspended
0.7027	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5844	Phase 1
0.7007	Intermediate Similarity	NPD4059	Approved
0.7006	Intermediate Similarity	NPD2801	Approved
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2329	Discontinued
0.7	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2934	Approved
0.6992	Remote Similarity	NPD2933	Approved
0.6988	Remote Similarity	NPD6559	Discontinued
0.6984	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7075	Discontinued
0.6974	Remote Similarity	NPD1511	Approved
0.697	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4307	Phase 2
0.6962	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6100	Approved
0.6959	Remote Similarity	NPD6099	Approved
0.6959	Remote Similarity	NPD2796	Approved
0.6943	Remote Similarity	NPD6844	Discontinued
0.6943	Remote Similarity	NPD1934	Approved
0.6934	Remote Similarity	NPD5691	Approved
0.6934	Remote Similarity	NPD4093	Discontinued
0.6929	Remote Similarity	NPD1755	Approved
0.6923	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3882	Suspended
0.6918	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7610	Discontinued
0.6909	Remote Similarity	NPD6020	Phase 2
0.6906	Remote Similarity	NPD1611	Approved
0.6906	Remote Similarity	NPD3092	Approved
0.6899	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3748	Approved
0.6887	Remote Similarity	NPD4628	Phase 3
0.6886	Remote Similarity	NPD5029	Approved
0.6886	Remote Similarity	NPD5031	Approved
0.6886	Remote Similarity	NPD5027	Approved
0.6884	Remote Similarity	NPD3095	Discontinued
0.6883	Remote Similarity	NPD1512	Approved
0.688	Remote Similarity	NPD3495	Discontinued
0.6879	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6213	Phase 3
0.6879	Remote Similarity	NPD6212	Phase 3
0.6866	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2296	Approved
0.6855	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4060	Phase 1
0.6846	Remote Similarity	NPD2531	Phase 2
0.6846	Remote Similarity	NPD2438	Suspended
0.6845	Remote Similarity	NPD5034	Approved
0.6845	Remote Similarity	NPD5028	Approved
0.6845	Remote Similarity	NPD36	Approved
0.6845	Remote Similarity	NPD4955	Approved
0.6845	Remote Similarity	NPD5026	Approved
0.6845	Remote Similarity	NPD4954	Approved
0.6842	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6535	Approved
0.6839	Remote Similarity	NPD6534	Approved
0.6835	Remote Similarity	NPD4879	Approved
0.6831	Remote Similarity	NPD3094	Phase 2
0.6821	Remote Similarity	NPD2800	Approved
0.6818	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6599	Discontinued
0.6809	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1809	Phase 2
0.679	Remote Similarity	NPD5494	Approved
0.6786	Remote Similarity	NPD5030	Phase 2
0.6781	Remote Similarity	NPD8032	Phase 2
0.6781	Remote Similarity	NPD520	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