NPASS Compound

Structure

NPC472406 OpenBabel07101718182D 23 25 0 0 1 0 0 0 0 0999 V2000 5.2812 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -2.8090 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 3 1 0 0 0 0 2 22 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 3 1 6 0 0 0 14 15 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.14
Volume:	334.086
LogP:	5.059
LogD:	4.18
LogS:	-6.101
# Rotatable Bonds:	6
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.587
Synthetic Accessibility Score:	2.754
Fsp3:	0.25
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:	-4.777
MDCK Permeability:	1.8551812900113873e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.066

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	98.78911590576172%
Volume Distribution (VD):	0.598
Pgp-substrate:	1.140970230102539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.975
CYP2C19-substrate:	0.127
CYP2C9-inhibitor:	0.95
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.595
CYP2D6-substrate:	0.523
CYP3A4-inhibitor:	0.824
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	6.661
Half-life (T1/2):	0.108

ADMET: Toxicity

hERG Blockers:	0.189
Human Hepatotoxicity (H-HT):	0.092
Drug-inuced Liver Injury (DILI):	0.813
AMES Toxicity:	0.277
Rat Oral Acute Toxicity:	0.759
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.084
Carcinogencity:	0.535
Eye Corrosion:	0.003
Eye Irritation:	0.738
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC472406

Natural Product ID:	NPC472406
*Common Name:**	XEXMYXBGTYEPEE-CQSZACIVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XEXMYXBGTYEPEE-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C20H20O3/c1-3-14(15-7-5-4-6-8-15)13-18(21)16-9-10-19-17(11-12-23-19)20(16)22-2/h4-12,14H,3,13H2,1-2H3/t14-/m1/s1
SMILES:	CC[C@@H](c1ccccc1)CC(=O)c1ccc2c(c1OC)cco2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3401054
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO19856	Millettia pulchra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25630222]
NPO19856	Millettia pulchra	Species	Fabaceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Ratio	=	2.07	n.a.	PMID[482517]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	92.0	%	PMID[482517]

☑ 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 NPC472406 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	472
0.1-0.2	1782
0.2-0.3	4348
0.3-0.4	11213
0.4-0.5	7236
0.5-0.6	4554
0.6-0.7	5890
0.7-0.8	4953
0.8-0.85	1723
0.85-0.9	462
0.9-0.95	59
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC198427
0.9589	High Similarity	NPC135303
0.9589	High Similarity	NPC148423
0.9586	High Similarity	NPC306788
0.9459	High Similarity	NPC263676
0.9459	High Similarity	NPC38361
0.9459	High Similarity	NPC130015
0.9448	High Similarity	NPC190572
0.9396	High Similarity	NPC41719
0.9392	High Similarity	NPC116604
0.9392	High Similarity	NPC472407
0.9333	High Similarity	NPC233776
0.9272	High Similarity	NPC247677
0.9272	High Similarity	NPC160015
0.9211	High Similarity	NPC260902
0.9211	High Similarity	NPC296957
0.9195	High Similarity	NPC191104
0.9178	High Similarity	NPC17262
0.915	High Similarity	NPC476350
0.915	High Similarity	NPC476349
0.9139	High Similarity	NPC213608
0.9139	High Similarity	NPC1477
0.9128	High Similarity	NPC226644
0.9128	High Similarity	NPC88445
0.9128	High Similarity	NPC37226
0.9091	High Similarity	NPC29638
0.9073	High Similarity	NPC67654
0.9073	High Similarity	NPC5871
0.9073	High Similarity	NPC253872
0.906	High Similarity	NPC135325
0.9054	High Similarity	NPC51641
0.9054	High Similarity	NPC300267
0.9038	High Similarity	NPC65846
0.9026	High Similarity	NPC40583
0.9013	High Similarity	NPC122365
0.9007	High Similarity	NPC156244
0.9007	High Similarity	NPC170169
0.9	High Similarity	NPC296030
0.9	High Similarity	NPC39929
0.8994	High Similarity	NPC190351
0.8993	High Similarity	NPC74539
0.8993	High Similarity	NPC304443
0.8993	High Similarity	NPC130581
0.8993	High Similarity	NPC12148
0.8986	High Similarity	NPC246903
0.8974	High Similarity	NPC193998
0.8961	High Similarity	NPC65504
0.8954	High Similarity	NPC198490
0.8954	High Similarity	NPC148938
0.894	High Similarity	NPC230713
0.894	High Similarity	NPC78335
0.8933	High Similarity	NPC266743
0.8926	High Similarity	NPC210826
0.8919	High Similarity	NPC225884
0.8917	High Similarity	NPC109180
0.8912	High Similarity	NPC22467
0.891	High Similarity	NPC304387
0.8903	High Similarity	NPC250076
0.8889	High Similarity	NPC183874
0.8889	High Similarity	NPC235333
0.8874	High Similarity	NPC178202
0.8859	High Similarity	NPC208584
0.8859	High Similarity	NPC230943
0.8854	High Similarity	NPC219861
0.8851	High Similarity	NPC166858
0.8851	High Similarity	NPC51146
0.8851	High Similarity	NPC313036
0.8839	High Similarity	NPC96342
0.8839	High Similarity	NPC269495
0.8839	High Similarity	NPC246647
0.8839	High Similarity	NPC212967
0.8839	High Similarity	NPC164110
0.8831	High Similarity	NPC213936
0.8831	High Similarity	NPC297531
0.8824	High Similarity	NPC207624
0.8808	High Similarity	NPC39195
0.8808	High Similarity	NPC272194
0.8797	High Similarity	NPC472581
0.8792	High Similarity	NPC262935
0.8792	High Similarity	NPC172182
0.8792	High Similarity	NPC251182
0.8792	High Similarity	NPC302181
0.8784	High Similarity	NPC254010
0.8774	High Similarity	NPC180924
0.8774	High Similarity	NPC474386
0.8766	High Similarity	NPC472462
0.8758	High Similarity	NPC193976
0.8758	High Similarity	NPC131866
0.8758	High Similarity	NPC115324
0.8758	High Similarity	NPC23668
0.8758	High Similarity	NPC106372
0.8758	High Similarity	NPC58668
0.875	High Similarity	NPC37208
0.875	High Similarity	NPC247743
0.875	High Similarity	NPC317492
0.875	High Similarity	NPC221868
0.8742	High Similarity	NPC17816
0.8742	High Similarity	NPC136641
0.8742	High Similarity	NPC38914
0.8742	High Similarity	NPC308200
0.8726	High Similarity	NPC49009
0.8726	High Similarity	NPC260296
0.8726	High Similarity	NPC115432
0.8725	High Similarity	NPC53192
0.8718	High Similarity	NPC268360
0.8718	High Similarity	NPC270044
0.8716	High Similarity	NPC28337
0.8712	High Similarity	NPC66804
0.871	High Similarity	NPC295608
0.871	High Similarity	NPC278010
0.871	High Similarity	NPC250769
0.8701	High Similarity	NPC142308
0.8699	High Similarity	NPC254741
0.8696	High Similarity	NPC41853
0.8693	High Similarity	NPC167576
0.8684	High Similarity	NPC145467
0.8684	High Similarity	NPC168085
0.8675	High Similarity	NPC299011
0.8671	High Similarity	NPC14822
0.8671	High Similarity	NPC472346
0.8671	High Similarity	NPC264293
0.8662	High Similarity	NPC472877
0.8662	High Similarity	NPC244750
0.8649	High Similarity	NPC262635
0.8649	High Similarity	NPC11566
0.8645	High Similarity	NPC131725
0.8639	High Similarity	NPC259685
0.8634	High Similarity	NPC241820
0.8634	High Similarity	NPC476459
0.8634	High Similarity	NPC167479
0.8627	High Similarity	NPC214493
0.8627	High Similarity	NPC471114
0.8621	High Similarity	NPC292998
0.8618	High Similarity	NPC471285
0.8609	High Similarity	NPC155144
0.8609	High Similarity	NPC184649
0.8609	High Similarity	NPC271288
0.8609	High Similarity	NPC311144
0.8609	High Similarity	NPC303185
0.8609	High Similarity	NPC98926
0.8609	High Similarity	NPC179970
0.8608	High Similarity	NPC303210
0.8608	High Similarity	NPC304839
0.8608	High Similarity	NPC95472
0.8608	High Similarity	NPC239270
0.8608	High Similarity	NPC220582
0.8608	High Similarity	NPC169
0.86	High Similarity	NPC96791
0.86	High Similarity	NPC470636
0.86	High Similarity	NPC226942
0.8591	High Similarity	NPC472409
0.8591	High Similarity	NPC470856
0.859	High Similarity	NPC99199
0.859	High Similarity	NPC474542
0.8589	High Similarity	NPC157522
0.8571	High Similarity	NPC321896
0.8571	High Similarity	NPC53640
0.8571	High Similarity	NPC13282
0.8571	High Similarity	NPC155882
0.8571	High Similarity	NPC472421
0.8571	High Similarity	NPC161196
0.8571	High Similarity	NPC277480
0.8571	High Similarity	NPC476185
0.8571	High Similarity	NPC471115
0.8571	High Similarity	NPC29777
0.8562	High Similarity	NPC38591
0.8562	High Similarity	NPC125269
0.8562	High Similarity	NPC155640
0.8553	High Similarity	NPC476153
0.8553	High Similarity	NPC74854
0.8553	High Similarity	NPC73320
0.8553	High Similarity	NPC215885
0.8553	High Similarity	NPC45124
0.8553	High Similarity	NPC30655
0.8553	High Similarity	NPC2416
0.8553	High Similarity	NPC477955
0.8552	High Similarity	NPC229646
0.8543	High Similarity	NPC113770
0.8537	High Similarity	NPC62640
0.8535	High Similarity	NPC470625
0.8526	High Similarity	NPC72370
0.8526	High Similarity	NPC42458
0.8526	High Similarity	NPC158261
0.8523	High Similarity	NPC477956
0.8523	High Similarity	NPC137009
0.8523	High Similarity	NPC472515
0.8519	High Similarity	NPC247973
0.8516	High Similarity	NPC474744
0.8516	High Similarity	NPC318424
0.8516	High Similarity	NPC474772
0.8516	High Similarity	NPC472423
0.8514	High Similarity	NPC157855
0.8514	High Similarity	NPC62735
0.8509	High Similarity	NPC37183
0.8509	High Similarity	NPC291110
0.8503	High Similarity	NPC99854
0.8493	Intermediate Similarity	NPC223354
0.8491	Intermediate Similarity	NPC298093
0.8487	Intermediate Similarity	NPC110776
0.8487	Intermediate Similarity	NPC473015

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 NPC472406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	997
0.2-0.3	1569
0.3-0.4	2783
0.4-0.5	1858
0.5-0.6	1048
0.6-0.7	329
0.7-0.8	107
0.8-0.85	33
0.85-0.9	5
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8993	High Similarity	NPD920	Approved
0.8986	High Similarity	NPD642	Clinical (unspecified phase)
0.8851	High Similarity	NPD643	Clinical (unspecified phase)
0.8699	High Similarity	NPD2796	Approved
0.8671	High Similarity	NPD1247	Approved
0.8649	High Similarity	NPD1243	Approved
0.8491	Intermediate Similarity	NPD5494	Approved
0.8471	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7411	Suspended
0.8366	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD919	Approved
0.8267	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD2344	Approved
0.8221	Intermediate Similarity	NPD3926	Phase 2
0.8176	Intermediate Similarity	NPD7819	Suspended
0.8171	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3749	Approved
0.8129	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1240	Approved
0.8095	Intermediate Similarity	NPD6559	Discontinued
0.8092	Intermediate Similarity	NPD1549	Phase 2
0.8072	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6799	Approved
0.8063	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2309	Approved
0.8039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2800	Approved
0.8026	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1510	Phase 2
0.8	Intermediate Similarity	NPD1607	Approved
0.7987	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7963	Intermediate Similarity	NPD7768	Phase 2
0.7963	Intermediate Similarity	NPD3882	Suspended
0.7914	Intermediate Similarity	NPD7075	Discontinued
0.7908	Intermediate Similarity	NPD1471	Phase 3
0.7895	Intermediate Similarity	NPD2799	Discontinued
0.7888	Intermediate Similarity	NPD6801	Discontinued
0.7888	Intermediate Similarity	NPD6280	Approved
0.7888	Intermediate Similarity	NPD6279	Approved
0.7879	Intermediate Similarity	NPD6959	Discontinued
0.7831	Intermediate Similarity	NPD6808	Phase 2
0.7785	Intermediate Similarity	NPD2532	Approved
0.7785	Intermediate Similarity	NPD2534	Approved
0.7785	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD3748	Approved
0.7778	Intermediate Similarity	NPD1934	Approved
0.773	Intermediate Similarity	NPD2801	Approved
0.7727	Intermediate Similarity	NPD1551	Phase 2
0.7697	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7473	Discontinued
0.7683	Intermediate Similarity	NPD3817	Phase 2
0.7647	Intermediate Similarity	NPD3818	Discontinued
0.7633	Intermediate Similarity	NPD2403	Approved
0.763	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6232	Discontinued
0.7616	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1511	Approved
0.7603	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6832	Phase 2
0.7593	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD3750	Approved
0.7529	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6166	Phase 2
0.7529	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1512	Approved
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.747	Intermediate Similarity	NPD2296	Approved
0.7469	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2654	Approved
0.7467	Intermediate Similarity	NPD2798	Approved
0.7458	Intermediate Similarity	NPD8434	Phase 2
0.744	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3972	Approved
0.7425	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6651	Approved
0.741	Intermediate Similarity	NPD5760	Phase 2
0.741	Intermediate Similarity	NPD5761	Phase 2
0.74	Intermediate Similarity	NPD3267	Approved
0.74	Intermediate Similarity	NPD3266	Approved
0.7386	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5402	Approved
0.7365	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5403	Approved
0.7355	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5401	Approved
0.7342	Intermediate Similarity	NPD2346	Discontinued
0.7333	Intermediate Similarity	NPD1876	Approved
0.7312	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4628	Phase 3
0.7273	Intermediate Similarity	NPD3268	Approved
0.7257	Intermediate Similarity	NPD1729	Discontinued
0.7257	Intermediate Similarity	NPD7074	Phase 3
0.7255	Intermediate Similarity	NPD4908	Phase 1
0.723	Intermediate Similarity	NPD17	Approved
0.7222	Intermediate Similarity	NPD1241	Discontinued
0.7215	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5711	Approved
0.7209	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD7054	Approved
0.7186	Intermediate Similarity	NPD5890	Approved
0.7186	Intermediate Similarity	NPD5889	Approved
0.7182	Intermediate Similarity	NPD4287	Approved
0.7178	Intermediate Similarity	NPD7390	Discontinued
0.7174	Intermediate Similarity	NPD4361	Phase 2
0.7174	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6099	Approved
0.717	Intermediate Similarity	NPD6100	Approved
0.7159	Intermediate Similarity	NPD7472	Approved
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1610	Phase 2
0.7124	Intermediate Similarity	NPD1019	Discontinued
0.712	Intermediate Similarity	NPD4363	Phase 3
0.712	Intermediate Similarity	NPD4360	Phase 2
0.7119	Intermediate Similarity	NPD6797	Phase 2
0.7099	Intermediate Similarity	NPD7003	Approved
0.7086	Intermediate Similarity	NPD1608	Approved
0.7083	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7251	Discontinued
0.707	Intermediate Similarity	NPD943	Approved
0.7066	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD1203	Approved
0.7052	Intermediate Similarity	NPD7199	Phase 2
0.7047	Intermediate Similarity	NPD1651	Approved
0.7039	Intermediate Similarity	NPD7808	Phase 3
0.7039	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1933	Approved
0.7024	Intermediate Similarity	NPD6585	Discontinued
0.7022	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1465	Phase 2
0.7	Intermediate Similarity	NPD7033	Discontinued
0.6994	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD9717	Approved
0.6971	Remote Similarity	NPD5242	Approved
0.6971	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7458	Discontinued
0.6962	Remote Similarity	NPD3142	Approved
0.6962	Remote Similarity	NPD3140	Approved
0.6962	Remote Similarity	NPD4307	Phase 2
0.6962	Remote Similarity	NPD2979	Phase 3
0.6951	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3764	Approved
0.6943	Remote Similarity	NPD1296	Phase 2
0.6918	Remote Similarity	NPD6355	Discontinued
0.6914	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6005	Phase 3
0.6914	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6004	Phase 3
0.6914	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6002	Phase 3
0.6908	Remote Similarity	NPD1281	Approved
0.6906	Remote Similarity	NPD8313	Approved
0.6906	Remote Similarity	NPD8312	Approved
0.689	Remote Similarity	NPD7466	Approved
0.6889	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6273	Approved
0.6879	Remote Similarity	NPD4625	Phase 3
0.6871	Remote Similarity	NPD2424	Discontinued
0.6867	Remote Similarity	NPD1548	Phase 1
0.6862	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4288	Approved
0.6854	Remote Similarity	NPD3751	Discontinued
0.6852	Remote Similarity	NPD4476	Approved
0.6852	Remote Similarity	NPD4477	Approved
0.6848	Remote Similarity	NPD3887	Approved
0.6845	Remote Similarity	NPD3873	Phase 3
0.6845	Remote Similarity	NPD3869	Phase 3
0.6842	Remote Similarity	NPD37	Approved
0.6839	Remote Similarity	NPD1164	Approved
0.6836	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4661	Approved
0.6826	Remote Similarity	NPD4662	Approved
0.6821	Remote Similarity	NPD4967	Phase 2
0.6821	Remote Similarity	NPD4966	Approved
0.6821	Remote Similarity	NPD4965	Approved
0.6821	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3787	Discontinued
0.6813	Remote Similarity	NPD447	Suspended
0.6813	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5124	Phase 1
0.6813	Remote Similarity	NPD230	Phase 1
0.6813	Remote Similarity	NPD4622	Approved
0.6813	Remote Similarity	NPD4618	Approved
0.6811	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8455	Phase 2

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