NPASS Compound

Structure

NPC471927 OpenBabel07101719152D 27 31 0 0 1 0 0 0 0 0999 V2000 2.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 -1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6049 0.0694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0580 3.1533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8862 3.1001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8771 0.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3778 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5708 0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0532 -1.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 1.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3461 -0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1249 1.6238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3611 2.4194 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2779 -0.3789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0191 -1.3449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 1.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3482 2.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2438 -0.1201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7262 -2.0520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7036 3.5138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9801 1.8040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 12 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 6 17 1 0 0 0 0 7 8 2 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 13 5 1 6 0 0 0 13 21 1 0 0 0 0 14 3 1 6 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 7 1 1 0 0 0 15 22 1 0 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 6 0 0 0 18 11 1 1 0 0 0 18 22 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.18
Volume:	382.924
LogP:	5.09
LogD:	4.141
LogS:	-3.217
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	4.647
Fsp3:	0.522
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.174
MDCK Permeability:	1.1721123883035034e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.178
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.28
Plasma Protein Binding (PPB):	96.2499771118164%
Volume Distribution (VD):	0.298
Pgp-substrate:	3.941682815551758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.571
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.187
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.655
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.524
CYP2D6-substrate:	0.298
CYP3A4-inhibitor:	0.33
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	8.092
Half-life (T1/2):	0.938

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.678
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.705
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.877
Carcinogencity:	0.411
Eye Corrosion:	0.035
Eye Irritation:	0.217
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC471927

Natural Product ID:	NPC471927
*Common Name:**	WRFCXWWPRNBPHO-WZQJHFQRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WRFCXWWPRNBPHO-WZQJHFQRSA-N
Standard InCHI:	InChI=1S/C23H26O4/c24-19-9-4-12(10-20(19)25)2-1-3-14-15-7-8-16-17(23(26)27)6-5-13-11-18(14)22(15)21(13)16/h4-10,13-18,21-22,24-25H,1-3,11H2,(H,26,27)/t13-,14-,15-,16+,17-,18+,21-,22-/m1/s1
SMILES:	C1C2C=CC(C3C2C4C1C(C4C=C3)CCCC5=CC(=C(C=C5)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3298854
PubChem CID:	90645497
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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
NPO33120	beilschmiedia ferruginea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24901800]

☑ 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
Ki	2
Others	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2796	Individual Protein	Apoptosis regulator Bcl-X	Homo sapiens	Inhibition	=	39.0	%	PMID[494896]
NPT2796	Individual Protein	Apoptosis regulator Bcl-X	Homo sapiens	Ki	>	100000.0	nM	PMID[494896]
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	Inhibition	=	82.0	%	PMID[494896]
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	Ki	=	5200.0	nM	PMID[494896]

☑ 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 NPC471927 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	306
0.1-0.2	1342
0.2-0.3	2956
0.3-0.4	8931
0.4-0.5	11004
0.5-0.6	11468
0.6-0.7	6047
0.7-0.8	615
0.8-0.85	19
0.85-0.9	3
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC471924
0.9231	High Similarity	NPC471928
0.9231	High Similarity	NPC471925
0.9213	High Similarity	NPC471913
0.9153	High Similarity	NPC471926
0.8718	High Similarity	NPC222084
0.8583	High Similarity	NPC471929
0.8583	High Similarity	NPC471930
0.8583	High Similarity	NPC471935
0.85	High Similarity	NPC148969
0.8433	Intermediate Similarity	NPC231719
0.8433	Intermediate Similarity	NPC52968
0.8425	Intermediate Similarity	NPC15127
0.8361	Intermediate Similarity	NPC4665
0.8333	Intermediate Similarity	NPC472271
0.8293	Intermediate Similarity	NPC277394
0.8293	Intermediate Similarity	NPC299252
0.8293	Intermediate Similarity	NPC471936
0.8293	Intermediate Similarity	NPC61062
0.8248	Intermediate Similarity	NPC323601
0.8189	Intermediate Similarity	NPC322332
0.8175	Intermediate Similarity	NPC34634
0.8175	Intermediate Similarity	NPC265454
0.8167	Intermediate Similarity	NPC228343
0.8167	Intermediate Similarity	NPC254833
0.8162	Intermediate Similarity	NPC476393
0.816	Intermediate Similarity	NPC63126
0.8148	Intermediate Similarity	NPC43353
0.814	Intermediate Similarity	NPC288945
0.814	Intermediate Similarity	NPC85565
0.812	Intermediate Similarity	NPC243305
0.811	Intermediate Similarity	NPC98305
0.811	Intermediate Similarity	NPC236520
0.811	Intermediate Similarity	NPC294361
0.8095	Intermediate Similarity	NPC42657
0.8095	Intermediate Similarity	NPC473974
0.8095	Intermediate Similarity	NPC258366
0.8095	Intermediate Similarity	NPC31296
0.8095	Intermediate Similarity	NPC79933
0.8085	Intermediate Similarity	NPC189054
0.808	Intermediate Similarity	NPC175799
0.808	Intermediate Similarity	NPC200988
0.808	Intermediate Similarity	NPC610
0.808	Intermediate Similarity	NPC325295
0.808	Intermediate Similarity	NPC145023
0.808	Intermediate Similarity	NPC76308
0.8074	Intermediate Similarity	NPC68779
0.8074	Intermediate Similarity	NPC5310
0.8074	Intermediate Similarity	NPC176814
0.8074	Intermediate Similarity	NPC4982
0.8074	Intermediate Similarity	NPC300776
0.8031	Intermediate Similarity	NPC190501
0.8031	Intermediate Similarity	NPC318552
0.8029	Intermediate Similarity	NPC471152
0.8016	Intermediate Similarity	NPC86198
0.8	Intermediate Similarity	NPC471749
0.8	Intermediate Similarity	NPC476282
0.7984	Intermediate Similarity	NPC86900
0.7983	Intermediate Similarity	NPC239291
0.797	Intermediate Similarity	NPC30174
0.7958	Intermediate Similarity	NPC8102
0.7958	Intermediate Similarity	NPC66894
0.7953	Intermediate Similarity	NPC470214
0.7953	Intermediate Similarity	NPC470215
0.7953	Intermediate Similarity	NPC70084
0.7953	Intermediate Similarity	NPC109371
0.7939	Intermediate Similarity	NPC280767
0.7937	Intermediate Similarity	NPC278652
0.7917	Intermediate Similarity	NPC477814
0.7917	Intermediate Similarity	NPC1075
0.7917	Intermediate Similarity	NPC294902
0.7917	Intermediate Similarity	NPC1786
0.7907	Intermediate Similarity	NPC177291
0.7907	Intermediate Similarity	NPC194416
0.7899	Intermediate Similarity	NPC471511
0.7899	Intermediate Similarity	NPC308976
0.7886	Intermediate Similarity	NPC297657
0.7883	Intermediate Similarity	NPC113295
0.7863	Intermediate Similarity	NPC245561
0.7857	Intermediate Similarity	NPC29599
0.784	Intermediate Similarity	NPC120280
0.7836	Intermediate Similarity	NPC241354
0.7829	Intermediate Similarity	NPC241001
0.7829	Intermediate Similarity	NPC164852
0.7826	Intermediate Similarity	NPC90431
0.7823	Intermediate Similarity	NPC51698
0.7815	Intermediate Similarity	NPC196479
0.7812	Intermediate Similarity	NPC141791
0.7812	Intermediate Similarity	NPC263386
0.781	Intermediate Similarity	NPC293454
0.7805	Intermediate Similarity	NPC120982
0.7805	Intermediate Similarity	NPC226401
0.7805	Intermediate Similarity	NPC79793
0.7805	Intermediate Similarity	NPC174096
0.7805	Intermediate Similarity	NPC147634
0.7803	Intermediate Similarity	NPC53305
0.7803	Intermediate Similarity	NPC257589
0.7797	Intermediate Similarity	NPC52472
0.7794	Intermediate Similarity	NPC239302
0.7786	Intermediate Similarity	NPC163083
0.7778	Intermediate Similarity	NPC109955
0.7769	Intermediate Similarity	NPC201777
0.7769	Intermediate Similarity	NPC162935
0.7769	Intermediate Similarity	NPC249340
0.7769	Intermediate Similarity	NPC188677
0.7762	Intermediate Similarity	NPC228940
0.7761	Intermediate Similarity	NPC167463
0.776	Intermediate Similarity	NPC264558
0.7754	Intermediate Similarity	NPC252343
0.7752	Intermediate Similarity	NPC478121
0.775	Intermediate Similarity	NPC261573
0.775	Intermediate Similarity	NPC120719
0.775	Intermediate Similarity	NPC8931
0.775	Intermediate Similarity	NPC120693
0.7746	Intermediate Similarity	NPC477873
0.7746	Intermediate Similarity	NPC469447
0.7744	Intermediate Similarity	NPC127937
0.7744	Intermediate Similarity	NPC321561
0.7744	Intermediate Similarity	NPC92207
0.7742	Intermediate Similarity	NPC179002
0.7742	Intermediate Similarity	NPC187583
0.7742	Intermediate Similarity	NPC257430
0.7737	Intermediate Similarity	NPC327410
0.7734	Intermediate Similarity	NPC309434
0.7734	Intermediate Similarity	NPC328694
0.7734	Intermediate Similarity	NPC203124
0.773	Intermediate Similarity	NPC282291
0.773	Intermediate Similarity	NPC166137
0.773	Intermediate Similarity	NPC100675
0.773	Intermediate Similarity	NPC9218
0.7724	Intermediate Similarity	NPC326187
0.7724	Intermediate Similarity	NPC55617
0.7724	Intermediate Similarity	NPC62258
0.7721	Intermediate Similarity	NPC318799
0.7721	Intermediate Similarity	NPC198388
0.7714	Intermediate Similarity	NPC318575
0.771	Intermediate Similarity	NPC121168
0.7704	Intermediate Similarity	NPC64111
0.7704	Intermediate Similarity	NPC208536
0.7698	Intermediate Similarity	NPC221870
0.7698	Intermediate Similarity	NPC476699
0.7698	Intermediate Similarity	NPC7464
0.7692	Intermediate Similarity	NPC470848
0.7692	Intermediate Similarity	NPC259703
0.7692	Intermediate Similarity	NPC477207
0.7692	Intermediate Similarity	NPC32322
0.7692	Intermediate Similarity	NPC470849
0.7687	Intermediate Similarity	NPC156539
0.7687	Intermediate Similarity	NPC178048
0.7686	Intermediate Similarity	NPC13495
0.768	Intermediate Similarity	NPC131530
0.7676	Intermediate Similarity	NPC52664
0.7676	Intermediate Similarity	NPC253722
0.7676	Intermediate Similarity	NPC31751
0.7676	Intermediate Similarity	NPC253481
0.7674	Intermediate Similarity	NPC156654
0.7669	Intermediate Similarity	NPC3221
0.7669	Intermediate Similarity	NPC197832
0.7664	Intermediate Similarity	NPC61
0.7664	Intermediate Similarity	NPC18074
0.7664	Intermediate Similarity	NPC25581
0.7664	Intermediate Similarity	NPC5419
0.7656	Intermediate Similarity	NPC150919
0.7652	Intermediate Similarity	NPC285345
0.7652	Intermediate Similarity	NPC306100
0.7647	Intermediate Similarity	NPC285361
0.7647	Intermediate Similarity	NPC172673
0.7647	Intermediate Similarity	NPC223393
0.7642	Intermediate Similarity	NPC31274
0.7639	Intermediate Similarity	NPC53520
0.7638	Intermediate Similarity	NPC474967
0.7634	Intermediate Similarity	NPC160380
0.7634	Intermediate Similarity	NPC147654
0.7634	Intermediate Similarity	NPC38996
0.763	Intermediate Similarity	NPC226661
0.763	Intermediate Similarity	NPC46192
0.763	Intermediate Similarity	NPC234175
0.7626	Intermediate Similarity	NPC470990
0.7626	Intermediate Similarity	NPC311742
0.7626	Intermediate Similarity	NPC123988
0.7623	Intermediate Similarity	NPC317592
0.7623	Intermediate Similarity	NPC70843
0.7622	Intermediate Similarity	NPC273657
0.7622	Intermediate Similarity	NPC106920
0.7615	Intermediate Similarity	NPC470585
0.7612	Intermediate Similarity	NPC84076
0.7612	Intermediate Similarity	NPC303680
0.7612	Intermediate Similarity	NPC269598
0.7612	Intermediate Similarity	NPC90128
0.7609	Intermediate Similarity	NPC168799
0.7609	Intermediate Similarity	NPC471328
0.7609	Intermediate Similarity	NPC155209
0.7606	Intermediate Similarity	NPC473612
0.7603	Intermediate Similarity	NPC52087
0.76	Intermediate Similarity	NPC226250
0.7597	Intermediate Similarity	NPC311091
0.7597	Intermediate Similarity	NPC471033
0.7597	Intermediate Similarity	NPC275519
0.7597	Intermediate Similarity	NPC205502
0.7594	Intermediate Similarity	NPC474766

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 NPC471927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	857
0.2-0.3	1497
0.3-0.4	2846
0.4-0.5	2143
0.5-0.6	1251
0.6-0.7	265
0.7-0.8	24
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8175	Intermediate Similarity	NPD2932	Approved
0.8167	Intermediate Similarity	NPD3021	Approved
0.8167	Intermediate Similarity	NPD3022	Approved
0.8031	Intermediate Similarity	NPD3019	Approved
0.7801	Intermediate Similarity	NPD8166	Discontinued
0.7744	Intermediate Similarity	NPD258	Approved
0.7744	Intermediate Similarity	NPD257	Approved
0.7721	Intermediate Similarity	NPD6663	Approved
0.7687	Intermediate Similarity	NPD5736	Approved
0.7557	Intermediate Similarity	NPD3023	Approved
0.7557	Intermediate Similarity	NPD3026	Approved
0.7556	Intermediate Similarity	NPD9569	Approved
0.7538	Intermediate Similarity	NPD3024	Approved
0.7538	Intermediate Similarity	NPD3025	Approved
0.7536	Intermediate Similarity	NPD826	Approved
0.7536	Intermediate Similarity	NPD825	Approved
0.7417	Intermediate Similarity	NPD3020	Approved
0.7357	Intermediate Similarity	NPD274	Approved
0.7357	Intermediate Similarity	NPD275	Approved
0.7338	Intermediate Similarity	NPD259	Phase 1
0.7319	Intermediate Similarity	NPD9537	Phase 1
0.7319	Intermediate Similarity	NPD9536	Phase 1
0.7313	Intermediate Similarity	NPD9269	Phase 2
0.731	Intermediate Similarity	NPD4110	Phase 3
0.731	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3092	Approved
0.7234	Intermediate Similarity	NPD6355	Discontinued
0.7234	Intermediate Similarity	NPD555	Phase 2
0.7219	Intermediate Similarity	NPD7028	Phase 2
0.7218	Intermediate Similarity	NPD4059	Approved
0.7197	Intermediate Similarity	NPD3091	Approved
0.7167	Intermediate Similarity	NPD2860	Approved
0.7167	Intermediate Similarity	NPD2859	Approved
0.7163	Intermediate Similarity	NPD943	Approved
0.7153	Intermediate Similarity	NPD3094	Phase 2
0.7143	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7132	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD255	Approved
0.7099	Intermediate Similarity	NPD256	Approved
0.7092	Intermediate Similarity	NPD8032	Phase 2
0.7083	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2934	Approved
0.7083	Intermediate Similarity	NPD2933	Approved
0.708	Intermediate Similarity	NPD1283	Approved
0.7071	Intermediate Similarity	NPD7095	Approved
0.7054	Intermediate Similarity	NPD228	Approved
0.7047	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3620	Phase 2
0.7042	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD9570	Approved
0.7015	Intermediate Similarity	NPD9268	Approved
0.7008	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9379	Approved
0.7	Intermediate Similarity	NPD9377	Approved
0.6993	Remote Similarity	NPD230	Phase 1
0.6967	Remote Similarity	NPD288	Approved
0.6963	Remote Similarity	NPD3095	Discontinued
0.6947	Remote Similarity	NPD5283	Phase 1
0.6944	Remote Similarity	NPD6653	Approved
0.6934	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD4060	Phase 1
0.6918	Remote Similarity	NPD5406	Approved
0.6918	Remote Similarity	NPD5408	Approved
0.6918	Remote Similarity	NPD5405	Approved
0.6918	Remote Similarity	NPD7199	Phase 2
0.6918	Remote Similarity	NPD5404	Approved
0.6917	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9568	Approved
0.6906	Remote Similarity	NPD2797	Approved
0.6906	Remote Similarity	NPD1164	Approved
0.6901	Remote Similarity	NPD6798	Discontinued
0.6899	Remote Similarity	NPD6234	Discontinued
0.6899	Remote Similarity	NPD4750	Phase 3
0.6894	Remote Similarity	NPD2629	Approved
0.6887	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD844	Approved
0.6871	Remote Similarity	NPD7266	Discontinued
0.6867	Remote Similarity	NPD3300	Phase 2
0.6861	Remote Similarity	NPD1281	Approved
0.6861	Remote Similarity	NPD1201	Approved
0.6861	Remote Similarity	NPD1535	Discovery
0.686	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5647	Approved
0.6849	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5958	Discontinued
0.6818	Remote Similarity	NPD3455	Phase 2
0.6815	Remote Similarity	NPD1759	Phase 1
0.6813	Remote Similarity	NPD8127	Discontinued
0.6812	Remote Similarity	NPD1481	Phase 2
0.6809	Remote Similarity	NPD9494	Approved
0.6806	Remote Similarity	NPD4140	Approved
0.6803	Remote Similarity	NPD1693	Approved
0.6803	Remote Similarity	NPD2935	Discontinued
0.68	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.68	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD37	Approved
0.6788	Remote Similarity	NPD3847	Discontinued
0.6786	Remote Similarity	NPD1470	Approved
0.6783	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3268	Approved
0.6774	Remote Similarity	NPD9495	Approved
0.6763	Remote Similarity	NPD1755	Approved
0.6761	Remote Similarity	NPD2614	Approved
0.6741	Remote Similarity	NPD1758	Phase 1
0.6736	Remote Similarity	NPD6233	Phase 2
0.6733	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6273	Approved
0.6721	Remote Similarity	NPD845	Approved
0.6715	Remote Similarity	NPD4626	Approved
0.6715	Remote Similarity	NPD17	Approved
0.6714	Remote Similarity	NPD1876	Approved
0.6714	Remote Similarity	NPD5310	Approved
0.6714	Remote Similarity	NPD5311	Approved
0.6713	Remote Similarity	NPD3027	Phase 3
0.6693	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2234	Approved
0.6692	Remote Similarity	NPD9266	Approved
0.6692	Remote Similarity	NPD2229	Approved
0.6692	Remote Similarity	NPD2228	Approved
0.6692	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD74	Approved
0.6691	Remote Similarity	NPD1894	Discontinued
0.6691	Remote Similarity	NPD9545	Approved
0.669	Remote Similarity	NPD2979	Phase 3
0.669	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD3055	Approved
0.6667	Remote Similarity	NPD1242	Phase 1
0.6667	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD4966	Approved
0.6667	Remote Similarity	NPD3053	Approved
0.6667	Remote Similarity	NPD4965	Approved
0.6667	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1445	Approved
0.6667	Remote Similarity	NPD1444	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7685	Pre-registration
0.6644	Remote Similarity	NPD5763	Approved
0.6644	Remote Similarity	NPD5762	Approved
0.6643	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4093	Discontinued
0.6642	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1651	Approved
0.6641	Remote Similarity	NPD1792	Phase 2
0.6641	Remote Similarity	NPD5909	Discontinued
0.6623	Remote Similarity	NPD4628	Phase 3
0.6623	Remote Similarity	NPD3750	Approved
0.6622	Remote Similarity	NPD2799	Discontinued
0.6621	Remote Similarity	NPD4062	Phase 3
0.662	Remote Similarity	NPD4624	Approved
0.6618	Remote Similarity	NPD5536	Phase 2
0.6617	Remote Similarity	NPD5535	Approved
0.6617	Remote Similarity	NPD7635	Approved
0.6615	Remote Similarity	NPD2342	Discontinued
0.6615	Remote Similarity	NPD9263	Approved
0.6615	Remote Similarity	NPD9267	Approved
0.6615	Remote Similarity	NPD9264	Approved
0.6614	Remote Similarity	NPD846	Approved
0.6614	Remote Similarity	NPD940	Approved
0.6613	Remote Similarity	NPD1809	Phase 2
0.6612	Remote Similarity	NPD1089	Approved
0.6612	Remote Similarity	NPD1086	Approved
0.6612	Remote Similarity	NPD1090	Approved
0.661	Remote Similarity	NPD111	Approved
0.6606	Remote Similarity	NPD7228	Approved
0.6601	Remote Similarity	NPD1511	Approved
0.6594	Remote Similarity	NPD9384	Approved
0.6594	Remote Similarity	NPD9381	Approved
0.6587	Remote Similarity	NPD2066	Phase 3
0.6577	Remote Similarity	NPD2438	Suspended
0.6575	Remote Similarity	NPD6346	Approved
0.6573	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD9493	Approved
0.6541	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6005	Phase 3
0.6533	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6002	Phase 3
0.6533	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6004	Phase 3
0.6531	Remote Similarity	NPD447	Suspended
0.6529	Remote Similarity	NPD800	Approved
0.6525	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5585	Approved
0.6519	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5951	Approved
0.6516	Remote Similarity	NPD1512	Approved
0.6513	Remote Similarity	NPD3400	Discontinued
0.6513	Remote Similarity	NPD7003	Approved
0.6504	Remote Similarity	NPD1088	Approved
0.6503	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2798	Approved
0.6491	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4534	Discontinued
0.649	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD3136	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