NPASS Compound

Structure

NPC474517 OpenBabel07101718292D 21 24 0 0 0 0 0 0 0 0999 V2000 -3.3347 0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 -3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0259 -1.1031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3890 -1.5374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9683 -0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4686 -1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4686 -0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 -1.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2738 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 -1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6369 -0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 -0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 0.2728 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 1.1991 0.9972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 1.2728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1490 0.9888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	276.08
Volume:	288.301
LogP:	4.936
LogD:	3.191
LogS:	-4.677
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.61
Synthetic Accessibility Score:	2.597
Fsp3:	0.056
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:	-5.033
MDCK Permeability:	1.379648983856896e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	98.73357391357422%
Volume Distribution (VD):	0.402
Pgp-substrate:	1.7904024124145508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.492
CYP2C19-inhibitor:	0.822
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.798
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.761
CYP2D6-substrate:	0.678
CYP3A4-inhibitor:	0.319
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	3.455
Half-life (T1/2):	0.219

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.288
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.828
Rat Oral Acute Toxicity:	0.711
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.942
Carcinogencity:	0.924
Eye Corrosion:	0.035
Eye Irritation:	0.979
Respiratory Toxicity:	0.731

Download Data

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

Natural Product: NPC474517

Natural Product ID:	NPC474517
*Common Name:**	6,8-Dihydroxy-5-Methylbenzo[A]Phenalen-7-One
IUPAC Name:	6,8-dihydroxy-5-methylbenzo[a]phenalen-7-one
Synonyms:
Standard InCHIKey:	LGHMJRHHYVWCBH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O3/c1-9-8-10-4-2-5-11-12-6-3-7-13(19)15(12)18(21)16(14(10)11)17(9)20/h2-8,19-20H,1H3
SMILES:	CC1=CC2=C3C(=CC=C2)C4=C(C(=CC=C4)O)C(=O)C3=C1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470547
PubChem CID:	44575531
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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
NPO1872	Picramnia latifolia	Species	Picramniaceae	Eukaryota	n.a.	Peru	n.a.	PMID[15043409]
NPO1872	Picramnia latifolia	Species	Picramniaceae	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[549417]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[549417]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[549417]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[549417]

☑ 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 NPC474517 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	398
0.1-0.2	1775
0.2-0.3	3926
0.3-0.4	11437
0.4-0.5	7385
0.5-0.6	5876
0.6-0.7	7654
0.7-0.8	3797
0.8-0.85	323
0.85-0.9	104
0.9-0.95	20
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC72669
0.9435	High Similarity	NPC173978
0.9385	High Similarity	NPC283088
0.9313	High Similarity	NPC474813
0.9308	High Similarity	NPC287604
0.9308	High Similarity	NPC161964
0.9308	High Similarity	NPC472262
0.9242	High Similarity	NPC245923
0.9231	High Similarity	NPC225051
0.9219	High Similarity	NPC99731
0.9185	High Similarity	NPC239136
0.9185	High Similarity	NPC19631
0.9173	High Similarity	NPC13715
0.9141	High Similarity	NPC48248
0.9141	High Similarity	NPC282923
0.9118	High Similarity	NPC296752
0.9111	High Similarity	NPC246638
0.9098	High Similarity	NPC62272
0.9084	High Similarity	NPC314048
0.9077	High Similarity	NPC244699
0.9051	High Similarity	NPC10764
0.9023	High Similarity	NPC155211
0.9015	High Similarity	NPC50924
0.8978	High Similarity	NPC313047
0.8978	High Similarity	NPC295712
0.8978	High Similarity	NPC474203
0.8978	High Similarity	NPC451542
0.8976	High Similarity	NPC142956
0.8947	High Similarity	NPC80035
0.8939	High Similarity	NPC267205
0.8939	High Similarity	NPC53896
0.8939	High Similarity	NPC115458
0.8931	High Similarity	NPC205992
0.8923	High Similarity	NPC146647
0.8923	High Similarity	NPC276238
0.8923	High Similarity	NPC34414
0.8913	High Similarity	NPC227841
0.8906	High Similarity	NPC103540
0.8897	High Similarity	NPC96421
0.8881	High Similarity	NPC191976
0.8864	High Similarity	NPC58685
0.8855	High Similarity	NPC55949
0.8849	High Similarity	NPC12402
0.8846	High Similarity	NPC96024
0.8841	High Similarity	NPC174905
0.8841	High Similarity	NPC293545
0.8837	High Similarity	NPC160499
0.8828	High Similarity	NPC164014
0.8824	High Similarity	NPC242994
0.8824	High Similarity	NPC138099
0.8819	High Similarity	NPC176208
0.8819	High Similarity	NPC300274
0.8815	High Similarity	NPC471905
0.8815	High Similarity	NPC53206
0.8815	High Similarity	NPC53001
0.8815	High Similarity	NPC53414
0.8788	High Similarity	NPC41847
0.8759	High Similarity	NPC169452
0.8759	High Similarity	NPC225243
0.8759	High Similarity	NPC181560
0.875	High Similarity	NPC375356
0.875	High Similarity	NPC87723
0.875	High Similarity	NPC416
0.875	High Similarity	NPC61398
0.8741	High Similarity	NPC254847
0.8741	High Similarity	NPC272268
0.8731	High Similarity	NPC12070
0.8723	High Similarity	NPC37709
0.8723	High Similarity	NPC290194
0.8722	High Similarity	NPC70622
0.8705	High Similarity	NPC471682
0.8696	High Similarity	NPC91019
0.8696	High Similarity	NPC477275
0.8696	High Similarity	NPC106519
0.8692	High Similarity	NPC3224
0.8682	High Similarity	NPC199273
0.8676	High Similarity	NPC305060
0.8672	High Similarity	NPC307174
0.8671	High Similarity	NPC205766
0.8667	High Similarity	NPC249272
0.8657	High Similarity	NPC114183
0.8657	High Similarity	NPC52407
0.8652	High Similarity	NPC147250
0.8647	High Similarity	NPC85342
0.8643	High Similarity	NPC477913
0.8636	High Similarity	NPC92624
0.8633	High Similarity	NPC69755
0.8633	High Similarity	NPC193555
0.8633	High Similarity	NPC85310
0.8633	High Similarity	NPC469520
0.8633	High Similarity	NPC257644
0.8626	High Similarity	NPC176130
0.8626	High Similarity	NPC78364
0.8626	High Similarity	NPC84672
0.8626	High Similarity	NPC69424
0.8613	High Similarity	NPC4214
0.8611	High Similarity	NPC35
0.8603	High Similarity	NPC118919
0.8593	High Similarity	NPC166480
0.8593	High Similarity	NPC288089
0.8593	High Similarity	NPC44437
0.8593	High Similarity	NPC270899
0.8593	High Similarity	NPC282780
0.8592	High Similarity	NPC119767
0.8582	High Similarity	NPC471683
0.8582	High Similarity	NPC68441
0.8571	High Similarity	NPC199253
0.8571	High Similarity	NPC259942
0.8571	High Similarity	NPC136588
0.8561	High Similarity	NPC305845
0.8561	High Similarity	NPC204045
0.856	High Similarity	NPC477453
0.8551	High Similarity	NPC26924
0.8551	High Similarity	NPC1268
0.8551	High Similarity	NPC143438
0.855	High Similarity	NPC254492
0.855	High Similarity	NPC96915
0.854	High Similarity	NPC474110
0.854	High Similarity	NPC44960
0.8538	High Similarity	NPC152525
0.8538	High Similarity	NPC236189
0.8538	High Similarity	NPC68756
0.8529	High Similarity	NPC258502
0.8521	High Similarity	NPC271944
0.8521	High Similarity	NPC110882
0.8521	High Similarity	NPC85393
0.8511	High Similarity	NPC21599
0.8511	High Similarity	NPC193703
0.85	High Similarity	NPC135524
0.85	High Similarity	NPC474961
0.8489	Intermediate Similarity	NPC315578
0.8485	Intermediate Similarity	NPC72667
0.8472	Intermediate Similarity	NPC477221
0.8462	Intermediate Similarity	NPC472135
0.8462	Intermediate Similarity	NPC162751
0.8462	Intermediate Similarity	NPC52161
0.845	Intermediate Similarity	NPC154696
0.845	Intermediate Similarity	NPC120545
0.8444	Intermediate Similarity	NPC175738
0.8438	Intermediate Similarity	NPC285829
0.8438	Intermediate Similarity	NPC206778
0.8435	Intermediate Similarity	NPC226656
0.8435	Intermediate Similarity	NPC66029
0.8435	Intermediate Similarity	NPC66508
0.8433	Intermediate Similarity	NPC31799
0.8433	Intermediate Similarity	NPC108129
0.8429	Intermediate Similarity	NPC187843
0.8429	Intermediate Similarity	NPC110810
0.8429	Intermediate Similarity	NPC124365
0.8417	Intermediate Similarity	NPC190457
0.8409	Intermediate Similarity	NPC231774
0.8403	Intermediate Similarity	NPC290695
0.8403	Intermediate Similarity	NPC106524
0.8397	Intermediate Similarity	NPC234890
0.8397	Intermediate Similarity	NPC74507
0.8394	Intermediate Similarity	NPC161632
0.8394	Intermediate Similarity	NPC153088
0.8392	Intermediate Similarity	NPC314437
0.8392	Intermediate Similarity	NPC472134
0.8392	Intermediate Similarity	NPC143685
0.8385	Intermediate Similarity	NPC282577
0.8385	Intermediate Similarity	NPC91478
0.8385	Intermediate Similarity	NPC283514
0.8382	Intermediate Similarity	NPC294226
0.838	Intermediate Similarity	NPC79627
0.838	Intermediate Similarity	NPC48762
0.838	Intermediate Similarity	NPC471906
0.838	Intermediate Similarity	NPC244691
0.8372	Intermediate Similarity	NPC32322
0.8372	Intermediate Similarity	NPC259703
0.837	Intermediate Similarity	NPC93015
0.837	Intermediate Similarity	NPC471851
0.8369	Intermediate Similarity	NPC73061
0.8358	Intermediate Similarity	NPC278928
0.8358	Intermediate Similarity	NPC303910
0.8358	Intermediate Similarity	NPC171460
0.8357	Intermediate Similarity	NPC168471
0.8346	Intermediate Similarity	NPC471530
0.8345	Intermediate Similarity	NPC141368
0.8345	Intermediate Similarity	NPC329933
0.8333	Intermediate Similarity	NPC477454
0.8333	Intermediate Similarity	NPC161304
0.8333	Intermediate Similarity	NPC34802
0.8333	Intermediate Similarity	NPC141934
0.8333	Intermediate Similarity	NPC215593
0.8333	Intermediate Similarity	NPC193358
0.8322	Intermediate Similarity	NPC34482
0.8322	Intermediate Similarity	NPC170055
0.8321	Intermediate Similarity	NPC198014
0.832	Intermediate Similarity	NPC322239
0.831	Intermediate Similarity	NPC66593
0.8308	Intermediate Similarity	NPC198336
0.8298	Intermediate Similarity	NPC290550
0.8296	Intermediate Similarity	NPC27659
0.8296	Intermediate Similarity	NPC62219
0.8296	Intermediate Similarity	NPC31539
0.8296	Intermediate Similarity	NPC475741
0.8288	Intermediate Similarity	NPC315520
0.8288	Intermediate Similarity	NPC477914
0.8281	Intermediate Similarity	NPC328694

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 NPC474517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	985
0.2-0.3	1250
0.3-0.4	2839
0.4-0.5	2038
0.5-0.6	1140
0.6-0.7	404
0.7-0.8	88
0.8-0.85	2
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9194	High Similarity	NPD1201	Approved
0.9098	High Similarity	NPD5405	Approved
0.9098	High Similarity	NPD5408	Approved
0.9098	High Similarity	NPD5404	Approved
0.9098	High Similarity	NPD5406	Approved
0.8913	High Similarity	NPD7390	Discontinued
0.8906	High Similarity	NPD1470	Approved
0.8741	High Similarity	NPD1509	Clinical (unspecified phase)
0.8582	High Similarity	NPD7422	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD1164	Approved
0.8042	Intermediate Similarity	NPD7003	Approved
0.8015	Intermediate Similarity	NPD3019	Approved
0.7984	Intermediate Similarity	NPD2342	Discontinued
0.7922	Intermediate Similarity	NPD6959	Discontinued
0.7879	Intermediate Similarity	NPD2932	Approved
0.7852	Intermediate Similarity	NPD3226	Approved
0.7832	Intermediate Similarity	NPD2346	Discontinued
0.7786	Intermediate Similarity	NPD943	Approved
0.777	Intermediate Similarity	NPD3764	Approved
0.7756	Intermediate Similarity	NPD6232	Discontinued
0.7722	Intermediate Similarity	NPD7473	Discontinued
0.7687	Intermediate Similarity	NPD3300	Phase 2
0.7676	Intermediate Similarity	NPD1607	Approved
0.7639	Intermediate Similarity	NPD2935	Discontinued
0.7591	Intermediate Similarity	NPD1283	Approved
0.7586	Intermediate Similarity	NPD2344	Approved
0.7584	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5951	Approved
0.7548	Intermediate Similarity	NPD7768	Phase 2
0.7538	Intermediate Similarity	NPD7635	Approved
0.7537	Intermediate Similarity	NPD1651	Approved
0.7537	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1240	Approved
0.7484	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2798	Approved
0.7481	Intermediate Similarity	NPD2286	Discontinued
0.7481	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2799	Discontinued
0.7448	Intermediate Similarity	NPD1510	Phase 2
0.7448	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3750	Approved
0.7426	Intermediate Similarity	NPD3023	Approved
0.7426	Intermediate Similarity	NPD3026	Approved
0.7419	Intermediate Similarity	NPD7819	Suspended
0.7407	Intermediate Similarity	NPD3024	Approved
0.7407	Intermediate Similarity	NPD3025	Approved
0.7389	Intermediate Similarity	NPD3749	Approved
0.7386	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2309	Approved
0.7381	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1281	Approved
0.7365	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7008	Discontinued
0.7308	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7411	Suspended
0.7273	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD2313	Discontinued
0.7237	Intermediate Similarity	NPD2532	Approved
0.7237	Intermediate Similarity	NPD2534	Approved
0.7237	Intermediate Similarity	NPD2533	Approved
0.7231	Intermediate Similarity	NPD74	Approved
0.7231	Intermediate Similarity	NPD9266	Approved
0.723	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4626	Approved
0.7226	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD6663	Approved
0.72	Intermediate Similarity	NPD8166	Discontinued
0.7195	Intermediate Similarity	NPD5844	Phase 1
0.719	Intermediate Similarity	NPD6273	Approved
0.7186	Intermediate Similarity	NPD8313	Approved
0.7186	Intermediate Similarity	NPD8312	Approved
0.7185	Intermediate Similarity	NPD9493	Approved
0.7183	Intermediate Similarity	NPD5736	Approved
0.7181	Intermediate Similarity	NPD1549	Phase 2
0.7171	Intermediate Similarity	NPD1511	Approved
0.7154	Intermediate Similarity	NPD9267	Approved
0.7154	Intermediate Similarity	NPD9264	Approved
0.7154	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD9263	Approved
0.7143	Intermediate Similarity	NPD3020	Approved
0.7134	Intermediate Similarity	NPD1934	Approved
0.7134	Intermediate Similarity	NPD7177	Discontinued
0.712	Intermediate Similarity	NPD288	Approved
0.7095	Intermediate Similarity	NPD3748	Approved
0.7092	Intermediate Similarity	NPD1876	Approved
0.7083	Intermediate Similarity	NPD4625	Phase 3
0.708	Intermediate Similarity	NPD3091	Approved
0.7078	Intermediate Similarity	NPD1512	Approved
0.7071	Intermediate Similarity	NPD3972	Approved
0.7066	Intermediate Similarity	NPD6559	Discontinued
0.7047	Intermediate Similarity	NPD2796	Approved
0.7045	Intermediate Similarity	NPD4750	Phase 3
0.7044	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD844	Approved
0.704	Intermediate Similarity	NPD2859	Approved
0.704	Intermediate Similarity	NPD2860	Approved
0.7012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6166	Phase 2
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3092	Approved
0.6994	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6020	Phase 2
0.6981	Remote Similarity	NPD2801	Approved
0.6978	Remote Similarity	NPD4059	Approved
0.6977	Remote Similarity	NPD1929	Approved
0.6977	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1930	Approved
0.6963	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2933	Approved
0.696	Remote Similarity	NPD2934	Approved
0.6959	Remote Similarity	NPD8150	Discontinued
0.6957	Remote Similarity	NPD9545	Approved
0.6957	Remote Similarity	NPD7075	Discontinued
0.695	Remote Similarity	NPD4878	Approved
0.6939	Remote Similarity	NPD2979	Phase 3
0.6933	Remote Similarity	NPD6099	Approved
0.6933	Remote Similarity	NPD1551	Phase 2
0.6933	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1203	Approved
0.6917	Remote Similarity	NPD3022	Approved
0.6917	Remote Similarity	NPD3021	Approved
0.6912	Remote Similarity	NPD497	Approved
0.6908	Remote Similarity	NPD2800	Approved
0.6906	Remote Similarity	NPD4093	Discontinued
0.6906	Remote Similarity	NPD5691	Approved
0.6903	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1471	Phase 3
0.6884	Remote Similarity	NPD7610	Discontinued
0.6875	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4308	Phase 3
0.6863	Remote Similarity	NPD4628	Phase 3
0.6863	Remote Similarity	NPD3400	Discontinued
0.6849	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9261	Approved
0.6838	Remote Similarity	NPD496	Approved
0.6838	Remote Similarity	NPD498	Approved
0.6838	Remote Similarity	NPD495	Approved
0.6832	Remote Similarity	NPD2296	Approved
0.6831	Remote Similarity	NPD1608	Approved
0.6822	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1242	Phase 1
0.6818	Remote Similarity	NPD6534	Approved
0.6818	Remote Similarity	NPD6535	Approved
0.6806	Remote Similarity	NPD2797	Approved
0.6806	Remote Similarity	NPD3094	Phase 2
0.6803	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD411	Approved
0.6797	Remote Similarity	NPD1243	Approved
0.6794	Remote Similarity	NPD1237	Approved
0.6792	Remote Similarity	NPD6599	Discontinued
0.679	Remote Similarity	NPD3882	Suspended
0.6788	Remote Similarity	NPD9281	Approved
0.6772	Remote Similarity	NPD1809	Phase 2
0.6769	Remote Similarity	NPD940	Approved
0.6769	Remote Similarity	NPD846	Approved
0.6769	Remote Similarity	NPD1932	Approved
0.6768	Remote Similarity	NPD5494	Approved
0.6765	Remote Similarity	NPD5029	Approved
0.6765	Remote Similarity	NPD5027	Approved
0.6765	Remote Similarity	NPD5031	Approved
0.6757	Remote Similarity	NPD8032	Phase 2
0.6753	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD845	Approved
0.6738	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3095	Discontinued
0.6733	Remote Similarity	NPD6651	Approved
0.6731	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6780	Approved
0.6722	Remote Similarity	NPD6778	Approved
0.6722	Remote Similarity	NPD6782	Approved
0.6722	Remote Similarity	NPD6776	Approved
0.6722	Remote Similarity	NPD6777	Approved
0.6722	Remote Similarity	NPD6781	Approved
0.6722	Remote Similarity	NPD6779	Approved
0.6716	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD9717	Approved
0.6711	Remote Similarity	NPD2438	Suspended
0.6711	Remote Similarity	NPD4477	Approved
0.6711	Remote Similarity	NPD4476	Approved
0.6711	Remote Similarity	NPD2531	Phase 2
0.6711	Remote Similarity	NPD4060	Phase 1
0.671	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6801	Discontinued
0.6704	Remote Similarity	NPD7700	Phase 2
0.6704	Remote Similarity	NPD7699	Phase 2
0.6693	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1432	Clinical (unspecified phase)

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