NPASS Compound

Structure

NPC473942 OpenBabel07101718182D 28 30 0 0 0 0 0 0 0 0999 V2000 5.8630 -1.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0605 0.0464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8794 -1.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0550 -0.0582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8739 -1.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4727 -0.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4617 -0.9717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4562 -1.0762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 8 1 0 0 0 0 4 12 2 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 13 2 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 28 1 0 0 0 0 20 23 2 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.11
Volume:	381.27
LogP:	3.321
LogD:	3.132
LogS:	-5.11
# Rotatable Bonds:	6
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	2.999
Fsp3:	0.19
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:	-4.69
MDCK Permeability:	6.528990343213081e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.332
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.624
Plasma Protein Binding (PPB):	94.72476196289062%
Volume Distribution (VD):	0.299
Pgp-substrate:	1.7956962585449219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.729
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.938
CYP2C19-substrate:	0.498
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.103
CYP2D6-substrate:	0.671
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.73

ADMET: Excretion

Clearance (CL):	8.641
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.804
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.612
Skin Sensitization:	0.106
Carcinogencity:	0.098
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.392

Download Data

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

Natural Product: NPC473942

Natural Product ID:	NPC473942
*Common Name:**	ZBPAJHNLYKPXRJ-HTXNQAPBSA-N
IUPAC Name:	n.a.
Synonyms:	4,4'-Dimethoxyvulpinic Acid
Standard InCHIKey:	ZBPAJHNLYKPXRJ-HTXNQAPBSA-N
Standard InCHI:	InChI=1S/C21H18O7/c1-25-14-8-4-12(5-9-14)16-18(22)19(28-21(16)24)17(20(23)27-3)13-6-10-15(26-2)11-7-13/h4-11,24H,1-3H3/b19-17+
SMILES:	COc1ccc(cc1)/C(=C/1OC(=C(C1=O)c1ccc(cc1)OC)O)/C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455874
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO33337	scleroderma sp.	Species	Sclerodermataceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[16378381]

☑ 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
EC50	2
Others	2

Activity Type	# Activity
NON-MOLECULAR	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	8.0	mm	PMID[527153]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	90000.0	nM	PMID[527154]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	109000.0	nM	PMID[527154]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	54.0	ug	PMID[527154]

☑ 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 NPC473942 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	254
0.1-0.2	1344
0.2-0.3	3753
0.3-0.4	9437
0.4-0.5	9186
0.5-0.6	5241
0.6-0.7	11404
0.7-0.8	2035
0.8-0.85	35
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8678	High Similarity	NPC293424
0.8667	High Similarity	NPC19290
0.8651	High Similarity	NPC474476
0.8607	High Similarity	NPC264976
0.8583	High Similarity	NPC296526
0.8583	High Similarity	NPC51345
0.856	High Similarity	NPC14141
0.8547	High Similarity	NPC234639
0.8512	High Similarity	NPC128249
0.8448	Intermediate Similarity	NPC1065
0.8443	Intermediate Similarity	NPC469954
0.8374	Intermediate Similarity	NPC471033
0.8374	Intermediate Similarity	NPC311091
0.8372	Intermediate Similarity	NPC2596
0.8346	Intermediate Similarity	NPC89630
0.8296	Intermediate Similarity	NPC284409
0.8276	Intermediate Similarity	NPC38209
0.8264	Intermediate Similarity	NPC109241
0.824	Intermediate Similarity	NPC470092
0.8231	Intermediate Similarity	NPC217431
0.819	Intermediate Similarity	NPC298224
0.8182	Intermediate Similarity	NPC17693
0.814	Intermediate Similarity	NPC88403
0.8099	Intermediate Similarity	NPC23332
0.8083	Intermediate Similarity	NPC259554
0.8083	Intermediate Similarity	NPC79543
0.8077	Intermediate Similarity	NPC303680
0.8077	Intermediate Similarity	NPC90128
0.8077	Intermediate Similarity	NPC84076
0.8045	Intermediate Similarity	NPC125153
0.8029	Intermediate Similarity	NPC86087
0.8017	Intermediate Similarity	NPC21162
0.8017	Intermediate Similarity	NPC183648
0.8016	Intermediate Similarity	NPC61779
0.8015	Intermediate Similarity	NPC276466
0.8015	Intermediate Similarity	NPC71638
0.8015	Intermediate Similarity	NPC123722
0.8015	Intermediate Similarity	NPC151167
0.8015	Intermediate Similarity	NPC123228
0.8015	Intermediate Similarity	NPC64230
0.8015	Intermediate Similarity	NPC5018
0.8	Intermediate Similarity	NPC45104
0.7985	Intermediate Similarity	NPC173034
0.7984	Intermediate Similarity	NPC220540
0.7983	Intermediate Similarity	NPC70843
0.7971	Intermediate Similarity	NPC289690
0.7971	Intermediate Similarity	NPC288452
0.797	Intermediate Similarity	NPC477694
0.797	Intermediate Similarity	NPC477705
0.797	Intermediate Similarity	NPC172673
0.7966	Intermediate Similarity	NPC109637
0.7966	Intermediate Similarity	NPC2518
0.7953	Intermediate Similarity	NPC474874
0.7939	Intermediate Similarity	NPC179777
0.7937	Intermediate Similarity	NPC152159
0.7937	Intermediate Similarity	NPC205502
0.7926	Intermediate Similarity	NPC202743
0.7923	Intermediate Similarity	NPC111088
0.7923	Intermediate Similarity	NPC288945
0.7923	Intermediate Similarity	NPC221798
0.792	Intermediate Similarity	NPC325646
0.792	Intermediate Similarity	NPC28951
0.792	Intermediate Similarity	NPC470860
0.7914	Intermediate Similarity	NPC28398
0.791	Intermediate Similarity	NPC477706
0.7903	Intermediate Similarity	NPC114144
0.7899	Intermediate Similarity	NPC13495
0.7895	Intermediate Similarity	NPC304622
0.7895	Intermediate Similarity	NPC238309
0.7887	Intermediate Similarity	NPC71210
0.7886	Intermediate Similarity	NPC199462
0.7883	Intermediate Similarity	NPC223616
0.7883	Intermediate Similarity	NPC90431
0.7879	Intermediate Similarity	NPC121104
0.7879	Intermediate Similarity	NPC223807
0.7869	Intermediate Similarity	NPC183700
0.7869	Intermediate Similarity	NPC473809
0.7863	Intermediate Similarity	NPC4164
0.7863	Intermediate Similarity	NPC53305
0.7863	Intermediate Similarity	NPC257589
0.7857	Intermediate Similarity	NPC240664
0.7857	Intermediate Similarity	NPC182475
0.7852	Intermediate Similarity	NPC186097
0.7852	Intermediate Similarity	NPC309717
0.7852	Intermediate Similarity	NPC475009
0.7852	Intermediate Similarity	NPC239302
0.7852	Intermediate Similarity	NPC164236
0.7852	Intermediate Similarity	NPC189106
0.7852	Intermediate Similarity	NPC475008
0.7852	Intermediate Similarity	NPC66384
0.7852	Intermediate Similarity	NPC112192
0.7852	Intermediate Similarity	NPC128348
0.7851	Intermediate Similarity	NPC281604
0.784	Intermediate Similarity	NPC23402
0.784	Intermediate Similarity	NPC322358
0.7836	Intermediate Similarity	NPC469929
0.7836	Intermediate Similarity	NPC2989
0.7836	Intermediate Similarity	NPC282230
0.7836	Intermediate Similarity	NPC183348
0.7836	Intermediate Similarity	NPC247779
0.7833	Intermediate Similarity	NPC95178
0.7833	Intermediate Similarity	NPC29989
0.7833	Intermediate Similarity	NPC326447
0.7833	Intermediate Similarity	NPC69332
0.7833	Intermediate Similarity	NPC113457
0.782	Intermediate Similarity	NPC475017
0.782	Intermediate Similarity	NPC110313
0.782	Intermediate Similarity	NPC219923
0.7817	Intermediate Similarity	NPC470216
0.781	Intermediate Similarity	NPC477301
0.781	Intermediate Similarity	NPC311742
0.7803	Intermediate Similarity	NPC92207
0.7803	Intermediate Similarity	NPC127937
0.7794	Intermediate Similarity	NPC205915
0.7794	Intermediate Similarity	NPC477536
0.7787	Intermediate Similarity	NPC474272
0.7787	Intermediate Similarity	NPC88141
0.7786	Intermediate Similarity	NPC56332
0.7778	Intermediate Similarity	NPC196979
0.7778	Intermediate Similarity	NPC15083
0.7778	Intermediate Similarity	NPC470976
0.7778	Intermediate Similarity	NPC470977
0.777	Intermediate Similarity	NPC475104
0.7769	Intermediate Similarity	NPC291189
0.7769	Intermediate Similarity	NPC69403
0.7769	Intermediate Similarity	NPC157473
0.7769	Intermediate Similarity	NPC151530
0.7761	Intermediate Similarity	NPC241354
0.7761	Intermediate Similarity	NPC211120
0.7761	Intermediate Similarity	NPC473019
0.7761	Intermediate Similarity	NPC66246
0.7761	Intermediate Similarity	NPC170546
0.7754	Intermediate Similarity	NPC230968
0.7754	Intermediate Similarity	NPC102260
0.7752	Intermediate Similarity	NPC471877
0.775	Intermediate Similarity	NPC227255
0.775	Intermediate Similarity	NPC473855
0.7746	Intermediate Similarity	NPC304956
0.7746	Intermediate Similarity	NPC46880
0.7744	Intermediate Similarity	NPC293387
0.7744	Intermediate Similarity	NPC78061
0.7744	Intermediate Similarity	NPC159987
0.7744	Intermediate Similarity	NPC264428
0.7744	Intermediate Similarity	NPC122359
0.7742	Intermediate Similarity	NPC48525
0.7737	Intermediate Similarity	NPC56031
0.7737	Intermediate Similarity	NPC82225
0.7737	Intermediate Similarity	NPC18877
0.7737	Intermediate Similarity	NPC312318
0.7737	Intermediate Similarity	NPC5310
0.7737	Intermediate Similarity	NPC159623
0.7737	Intermediate Similarity	NPC27643
0.7737	Intermediate Similarity	NPC20560
0.7737	Intermediate Similarity	NPC144051
0.7737	Intermediate Similarity	NPC300776
0.7737	Intermediate Similarity	NPC188646
0.7737	Intermediate Similarity	NPC175098
0.7737	Intermediate Similarity	NPC176814
0.7737	Intermediate Similarity	NPC204960
0.7737	Intermediate Similarity	NPC28753
0.7737	Intermediate Similarity	NPC68779
0.7737	Intermediate Similarity	NPC192304
0.7737	Intermediate Similarity	NPC139813
0.7737	Intermediate Similarity	NPC263670
0.7737	Intermediate Similarity	NPC4982
0.7737	Intermediate Similarity	NPC242294
0.7737	Intermediate Similarity	NPC337373
0.7737	Intermediate Similarity	NPC472365
0.7737	Intermediate Similarity	NPC294593
0.7731	Intermediate Similarity	NPC179686
0.773	Intermediate Similarity	NPC474037
0.7727	Intermediate Similarity	NPC280767
0.7727	Intermediate Similarity	NPC2771
0.7724	Intermediate Similarity	NPC287294
0.7721	Intermediate Similarity	NPC153453
0.7721	Intermediate Similarity	NPC262359
0.7717	Intermediate Similarity	NPC280001
0.7717	Intermediate Similarity	NPC185738
0.7714	Intermediate Similarity	NPC470855
0.7714	Intermediate Similarity	NPC71903
0.7714	Intermediate Similarity	NPC276905
0.771	Intermediate Similarity	NPC257976
0.771	Intermediate Similarity	NPC242372
0.771	Intermediate Similarity	NPC93730
0.771	Intermediate Similarity	NPC4181
0.771	Intermediate Similarity	NPC164778
0.7708	Intermediate Similarity	NPC153758
0.7705	Intermediate Similarity	NPC206341
0.7705	Intermediate Similarity	NPC31274
0.7704	Intermediate Similarity	NPC245395
0.7704	Intermediate Similarity	NPC66905
0.7698	Intermediate Similarity	NPC72452
0.7698	Intermediate Similarity	NPC188907
0.7698	Intermediate Similarity	NPC61546
0.7698	Intermediate Similarity	NPC477534
0.7692	Intermediate Similarity	NPC258671
0.7692	Intermediate Similarity	NPC471305
0.7692	Intermediate Similarity	NPC194416
0.7692	Intermediate Similarity	NPC175298
0.7692	Intermediate Similarity	NPC177291

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 NPC473942 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	903
0.2-0.3	1284
0.3-0.4	2418
0.4-0.5	2186
0.5-0.6	1380
0.6-0.7	634
0.7-0.8	104
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8244	Intermediate Similarity	NPD6798	Discontinued
0.8195	Intermediate Similarity	NPD6355	Discontinued
0.8182	Intermediate Similarity	NPD4062	Phase 3
0.8182	Intermediate Similarity	NPD6233	Phase 2
0.8175	Intermediate Similarity	NPD3847	Discontinued
0.8115	Intermediate Similarity	NPD1241	Discontinued
0.808	Intermediate Similarity	NPD1894	Discontinued
0.8077	Intermediate Similarity	NPD2798	Approved
0.8047	Intermediate Similarity	NPD3972	Approved
0.7943	Intermediate Similarity	NPD6799	Approved
0.7943	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD1876	Approved
0.7923	Intermediate Similarity	NPD1283	Approved
0.7907	Intermediate Similarity	NPD1481	Phase 2
0.7886	Intermediate Similarity	NPD5535	Approved
0.7883	Intermediate Similarity	NPD2799	Discontinued
0.7863	Intermediate Similarity	NPD2797	Approved
0.7836	Intermediate Similarity	NPD3268	Approved
0.7836	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD3134	Approved
0.7829	Intermediate Similarity	NPD1281	Approved
0.7829	Intermediate Similarity	NPD1535	Discovery
0.7826	Intermediate Similarity	NPD2935	Discontinued
0.782	Intermediate Similarity	NPD6832	Phase 2
0.7801	Intermediate Similarity	NPD3887	Approved
0.7801	Intermediate Similarity	NPD2354	Approved
0.7786	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2353	Approved
0.777	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD1358	Approved
0.7761	Intermediate Similarity	NPD7095	Approved
0.776	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD1651	Approved
0.7727	Intermediate Similarity	NPD3267	Approved
0.7727	Intermediate Similarity	NPD3266	Approved
0.7717	Intermediate Similarity	NPD5536	Phase 2
0.7634	Intermediate Similarity	NPD1608	Approved
0.7619	Intermediate Similarity	NPD6599	Discontinued
0.7606	Intermediate Similarity	NPD4628	Phase 3
0.7594	Intermediate Similarity	NPD1203	Approved
0.7591	Intermediate Similarity	NPD2979	Phase 3
0.7589	Intermediate Similarity	NPD4534	Discontinued
0.7589	Intermediate Similarity	NPD5958	Discontinued
0.7586	Intermediate Similarity	NPD5049	Phase 3
0.7576	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD2313	Discontinued
0.7556	Intermediate Similarity	NPD2614	Approved
0.7551	Intermediate Similarity	NPD7458	Discontinued
0.7538	Intermediate Similarity	NPD17	Approved
0.7538	Intermediate Similarity	NPD4626	Approved
0.7536	Intermediate Similarity	NPD1933	Approved
0.7536	Intermediate Similarity	NPD4340	Discontinued
0.7534	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD2067	Discontinued
0.75	Intermediate Similarity	NPD9717	Approved
0.7483	Intermediate Similarity	NPD7003	Approved
0.7467	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1240	Approved
0.7464	Intermediate Similarity	NPD4060	Phase 1
0.7462	Intermediate Similarity	NPD5585	Approved
0.7447	Intermediate Similarity	NPD4476	Approved
0.7447	Intermediate Similarity	NPD4477	Approved
0.7445	Intermediate Similarity	NPD3764	Approved
0.7424	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3817	Phase 2
0.7415	Intermediate Similarity	NPD5403	Approved
0.74	Intermediate Similarity	NPD6801	Discontinued
0.7397	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5401	Approved
0.7394	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8032	Phase 2
0.7388	Intermediate Similarity	NPD3225	Approved
0.7379	Intermediate Similarity	NPD7440	Discontinued
0.7376	Intermediate Similarity	NPD4308	Phase 3
0.7376	Intermediate Similarity	NPD3748	Approved
0.7364	Intermediate Similarity	NPD9493	Approved
0.7361	Intermediate Similarity	NPD3750	Approved
0.7361	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5451	Approved
0.7357	Intermediate Similarity	NPD1607	Approved
0.7348	Intermediate Similarity	NPD3496	Discontinued
0.7347	Intermediate Similarity	NPD6273	Approved
0.7338	Intermediate Similarity	NPD4307	Phase 2
0.7328	Intermediate Similarity	NPD5691	Approved
0.7324	Intermediate Similarity	NPD2531	Phase 2
0.7324	Intermediate Similarity	NPD2438	Suspended
0.732	Intermediate Similarity	NPD7075	Discontinued
0.7305	Intermediate Similarity	NPD7097	Phase 1
0.7292	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD2684	Approved
0.7279	Intermediate Similarity	NPD5647	Approved
0.7273	Intermediate Similarity	NPD2344	Approved
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7266	Intermediate Similarity	NPD5283	Phase 1
0.7259	Intermediate Similarity	NPD196	Phase 1
0.7254	Intermediate Similarity	NPD7033	Discontinued
0.7254	Intermediate Similarity	NPD1510	Phase 2
0.7246	Intermediate Similarity	NPD5163	Phase 2
0.7241	Intermediate Similarity	NPD4110	Phase 3
0.7241	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5909	Discontinued
0.7226	Intermediate Similarity	NPD454	Approved
0.7222	Intermediate Similarity	NPD2897	Discontinued
0.7222	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7411	Suspended
0.7214	Intermediate Similarity	NPD3142	Approved
0.7214	Intermediate Similarity	NPD3140	Approved
0.7203	Intermediate Similarity	NPD2796	Approved
0.7203	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1238	Approved
0.7188	Intermediate Similarity	NPD7843	Approved
0.7185	Intermediate Similarity	NPD4359	Approved
0.7177	Intermediate Similarity	NPD9697	Approved
0.7164	Intermediate Similarity	NPD422	Phase 1
0.7163	Intermediate Similarity	NPD4618	Approved
0.7163	Intermediate Similarity	NPD4622	Approved
0.7153	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1019	Discontinued
0.7153	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1471	Phase 3
0.7152	Intermediate Similarity	NPD7028	Phase 2
0.7143	Intermediate Similarity	NPD2933	Approved
0.7143	Intermediate Similarity	NPD1778	Approved
0.7143	Intermediate Similarity	NPD2934	Approved
0.7143	Intermediate Similarity	NPD3882	Suspended
0.7124	Intermediate Similarity	NPD7819	Suspended
0.7103	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1549	Phase 2
0.7097	Intermediate Similarity	NPD6971	Discontinued
0.7083	Intermediate Similarity	NPD2239	Approved
0.7083	Intermediate Similarity	NPD2860	Approved
0.7083	Intermediate Similarity	NPD1551	Phase 2
0.7083	Intermediate Similarity	NPD2240	Approved
0.7083	Intermediate Similarity	NPD2859	Approved
0.708	Intermediate Similarity	NPD6362	Approved
0.708	Intermediate Similarity	NPD987	Approved
0.7078	Intermediate Similarity	NPD5402	Approved
0.7075	Intermediate Similarity	NPD2309	Approved
0.7071	Intermediate Similarity	NPD1296	Phase 2
0.7063	Intermediate Similarity	NPD1536	Approved
0.7063	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5688	Approved
0.7063	Intermediate Similarity	NPD5689	Approved
0.7031	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2788	Approved
0.7023	Intermediate Similarity	NPD6387	Discontinued
0.7023	Intermediate Similarity	NPD709	Approved
0.7023	Intermediate Similarity	NPD7157	Approved
0.7008	Intermediate Similarity	NPD2182	Approved
0.7	Intermediate Similarity	NPD2598	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3274	Phase 2
0.6993	Remote Similarity	NPD958	Approved
0.6984	Remote Similarity	NPD968	Approved
0.6981	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD9494	Approved
0.6972	Remote Similarity	NPD4140	Approved
0.6966	Remote Similarity	NPD1538	Phase 1
0.6966	Remote Similarity	NPD1519	Approved
0.6966	Remote Similarity	NPD1537	Approved
0.696	Remote Similarity	NPD1237	Approved
0.696	Remote Similarity	NPD164	Approved
0.6959	Remote Similarity	NPD6190	Approved
0.695	Remote Similarity	NPD411	Approved
0.6948	Remote Similarity	NPD37	Approved
0.6944	Remote Similarity	NPD1520	Approved
0.6944	Remote Similarity	NPD1521	Approved
0.6939	Remote Similarity	NPD1243	Approved
0.6934	Remote Similarity	NPD3685	Discontinued
0.6934	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3146	Approved
0.6923	Remote Similarity	NPD447	Suspended
0.6923	Remote Similarity	NPD1138	Approved
0.6923	Remote Similarity	NPD821	Approved
0.6923	Remote Similarity	NPD7768	Phase 2
0.6923	Remote Similarity	NPD1184	Approved
0.6918	Remote Similarity	NPD5762	Approved
0.6918	Remote Similarity	NPD5763	Approved
0.6917	Remote Similarity	NPD1202	Approved
0.6914	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6287	Discontinued
0.6911	Remote Similarity	NPD3020	Approved
0.6911	Remote Similarity	NPD2066	Phase 3
0.6908	Remote Similarity	NPD957	Approved
0.6908	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8455	Phase 2
0.6901	Remote Similarity	NPD4870	Approved
0.6894	Remote Similarity	NPD4198	Discontinued
0.6892	Remote Similarity	NPD8166	Discontinued
0.6889	Remote Similarity	NPD2667	Approved
0.6889	Remote Similarity	NPD5846	Approved
0.6889	Remote Similarity	NPD2668	Approved
0.6889	Remote Similarity	NPD2932	Approved
0.6889	Remote Similarity	NPD3019	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