NPASS Compound

Structure

NPC475784 OpenBabel07101718302D 28 31 0 0 1 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7172 -0.7739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 26 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 21 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 17 2 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 10 22 1 0 0 0 0 11 20 1 0 0 0 0 13 23 1 0 0 0 0 14 19 2 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 25 2 0 0 0 0 16 12 1 6 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 20 28 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.12
Volume:	377.986
LogP:	3.044
LogD:	2.632
LogS:	-4.325
# Rotatable Bonds:	3
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	3.841
Fsp3:	0.286
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:	-4.729
MDCK Permeability:	1.5536232240265235e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.106

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	92.0634765625%
Volume Distribution (VD):	1.08
Pgp-substrate:	8.655123710632324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.551
CYP1A2-substrate:	0.664
CYP2C19-inhibitor:	0.16
CYP2C19-substrate:	0.172
CYP2C9-inhibitor:	0.598
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.556
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	14.059
Half-life (T1/2):	0.494

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.902
Carcinogencity:	0.777
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC475784

Natural Product ID:	NPC475784
*Common Name:**	(2S)-5,7-Dihydroxy-2'-(Hydroxymethyl)-8'-Methoxy-2'-Methyl-2,6'-Bichroman-4-One
IUPAC Name:	(2S)-5,7-dihydroxy-2-[2-(hydroxymethyl)-8-methoxy-2-methylchromen-6-yl]-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	DNWBCRWFRVKNFW-BJQOMGFOSA-N
Standard InCHI:	InChI=1S/C21H20O7/c1-21(10-22)4-3-11-5-12(6-18(26-2)20(11)28-21)16-9-15(25)19-14(24)7-13(23)8-17(19)27-16/h3-8,16,22-24H,9-10H2,1-2H3/t16-,21?/m0/s1
SMILES:	CC1(C=CC2=C(O1)C(=CC(=C2)C3CC(=O)C4=C(C=C(C=C4O3)O)O)OC)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515537
PubChem CID:	25147600
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8526	Erythrina abyssinica	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	17900.0	nM	PMID[518879]

☑ 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 NPC475784 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	402
0.1-0.2	1589
0.2-0.3	3848
0.3-0.4	9558
0.4-0.5	8743
0.5-0.6	3344
0.6-0.7	4827
0.7-0.8	5481
0.8-0.85	2908
0.85-0.9	1566
0.9-0.95	365
0.95-1	66

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC474038
0.9868	High Similarity	NPC192686
0.9868	High Similarity	NPC284820
0.9868	High Similarity	NPC119209
0.9868	High Similarity	NPC473272
0.9868	High Similarity	NPC118256
0.9805	High Similarity	NPC472625
0.9804	High Similarity	NPC26326
0.9804	High Similarity	NPC472632
0.9803	High Similarity	NPC473990
0.974	High Similarity	NPC474033
0.974	High Similarity	NPC474034
0.9739	High Similarity	NPC174953
0.9737	High Similarity	NPC472598
0.9737	High Similarity	NPC27337
0.9737	High Similarity	NPC474055
0.9677	High Similarity	NPC186686
0.9675	High Similarity	NPC472634
0.9675	High Similarity	NPC471210
0.9673	High Similarity	NPC117418
0.9673	High Similarity	NPC53545
0.9671	High Similarity	NPC35038
0.9671	High Similarity	NPC195796
0.9671	High Similarity	NPC278778
0.9671	High Similarity	NPC291878
0.9613	High Similarity	NPC472635
0.9613	High Similarity	NPC474150
0.9613	High Similarity	NPC474162
0.9613	High Similarity	NPC476247
0.961	High Similarity	NPC282009
0.961	High Similarity	NPC287328
0.961	High Similarity	NPC472624
0.961	High Similarity	NPC472631
0.961	High Similarity	NPC472630
0.9608	High Similarity	NPC291508
0.9608	High Similarity	NPC471209
0.9608	High Similarity	NPC78071
0.9608	High Similarity	NPC52889
0.9605	High Similarity	NPC321779
0.9605	High Similarity	NPC226025
0.9605	High Similarity	NPC470327
0.9605	High Similarity	NPC477503
0.9605	High Similarity	NPC45849
0.9605	High Similarity	NPC200761
0.9554	High Similarity	NPC471213
0.9554	High Similarity	NPC43319
0.9551	High Similarity	NPC124038
0.9548	High Similarity	NPC471499
0.9548	High Similarity	NPC142252
0.9548	High Similarity	NPC471211
0.9548	High Similarity	NPC289771
0.9548	High Similarity	NPC471212
0.9548	High Similarity	NPC134783
0.9545	High Similarity	NPC74178
0.9545	High Similarity	NPC184755
0.9545	High Similarity	NPC187792
0.9545	High Similarity	NPC22192
0.9545	High Similarity	NPC204879
0.9542	High Similarity	NPC470328
0.9542	High Similarity	NPC209614
0.9542	High Similarity	NPC471985
0.9542	High Similarity	NPC472626
0.9539	High Similarity	NPC7989
0.9539	High Similarity	NPC213896
0.9539	High Similarity	NPC74924
0.9539	High Similarity	NPC472583
0.9539	High Similarity	NPC223701
0.9539	High Similarity	NPC18727
0.9539	High Similarity	NPC192083
0.9494	High Similarity	NPC218226
0.949	High Similarity	NPC293319
0.949	High Similarity	NPC62261
0.9487	High Similarity	NPC83922
0.9487	High Similarity	NPC472448
0.9484	High Similarity	NPC36217
0.9484	High Similarity	NPC470326
0.9484	High Similarity	NPC204290
0.9484	High Similarity	NPC328102
0.9481	High Similarity	NPC474681
0.9481	High Similarity	NPC223787
0.9481	High Similarity	NPC218313
0.9481	High Similarity	NPC183851
0.9481	High Similarity	NPC63454
0.9477	High Similarity	NPC259710
0.9477	High Similarity	NPC234255
0.9477	High Similarity	NPC217706
0.9477	High Similarity	NPC48579
0.9477	High Similarity	NPC207809
0.9477	High Similarity	NPC304207
0.9474	High Similarity	NPC471982
0.9474	High Similarity	NPC475790
0.9474	High Similarity	NPC56232
0.9474	High Similarity	NPC106976
0.9474	High Similarity	NPC219582
0.9474	High Similarity	NPC40033
0.9474	High Similarity	NPC150123
0.9474	High Similarity	NPC302950
0.9474	High Similarity	NPC161881
0.9474	High Similarity	NPC10807
0.9474	High Similarity	NPC236637
0.9474	High Similarity	NPC244583
0.947	High Similarity	NPC338131
0.947	High Similarity	NPC472633
0.9434	High Similarity	NPC288813
0.9434	High Similarity	NPC475212
0.943	High Similarity	NPC119589
0.943	High Similarity	NPC272502
0.943	High Similarity	NPC120593
0.9423	High Similarity	NPC165970
0.9423	High Similarity	NPC158188
0.9423	High Similarity	NPC198829
0.9423	High Similarity	NPC167678
0.9423	High Similarity	NPC113163
0.9423	High Similarity	NPC66618
0.9423	High Similarity	NPC305987
0.9423	High Similarity	NPC84324
0.9423	High Similarity	NPC288131
0.9423	High Similarity	NPC29876
0.9419	High Similarity	NPC95936
0.9419	High Similarity	NPC172202
0.9419	High Similarity	NPC284127
0.9419	High Similarity	NPC250214
0.9419	High Similarity	NPC476410
0.9416	High Similarity	NPC208152
0.9416	High Similarity	NPC133970
0.9416	High Similarity	NPC326037
0.9416	High Similarity	NPC6633
0.9416	High Similarity	NPC320825
0.9416	High Similarity	NPC282307
0.9416	High Similarity	NPC13858
0.9416	High Similarity	NPC170026
0.9416	High Similarity	NPC5322
0.9416	High Similarity	NPC472455
0.9416	High Similarity	NPC78492
0.9412	High Similarity	NPC170492
0.9412	High Similarity	NPC298692
0.9412	High Similarity	NPC248793
0.9412	High Similarity	NPC180301
0.9412	High Similarity	NPC469405
0.9408	High Similarity	NPC244577
0.9408	High Similarity	NPC474021
0.9408	High Similarity	NPC477897
0.9408	High Similarity	NPC289774
0.9408	High Similarity	NPC471677
0.9408	High Similarity	NPC474023
0.9408	High Similarity	NPC263384
0.9408	High Similarity	NPC471676
0.9408	High Similarity	NPC209846
0.9408	High Similarity	NPC472422
0.9408	High Similarity	NPC472420
0.9408	High Similarity	NPC328740
0.9371	High Similarity	NPC474024
0.9371	High Similarity	NPC477154
0.9371	High Similarity	NPC117854
0.9371	High Similarity	NPC6588
0.9367	High Similarity	NPC300053
0.9367	High Similarity	NPC108433
0.9367	High Similarity	NPC239752
0.9367	High Similarity	NPC275780
0.9367	High Similarity	NPC472450
0.9367	High Similarity	NPC50960
0.9363	High Similarity	NPC229632
0.9363	High Similarity	NPC201800
0.9363	High Similarity	NPC261470
0.9363	High Similarity	NPC194427
0.9363	High Similarity	NPC472964
0.9359	High Similarity	NPC471976
0.9359	High Similarity	NPC472902
0.9359	High Similarity	NPC474960
0.9359	High Similarity	NPC321399
0.9359	High Similarity	NPC101731
0.9359	High Similarity	NPC470183
0.9359	High Similarity	NPC471973
0.9359	High Similarity	NPC476980
0.9359	High Similarity	NPC299436
0.9355	High Similarity	NPC475267
0.9355	High Similarity	NPC471479
0.9355	High Similarity	NPC48208
0.9355	High Similarity	NPC52530
0.9355	High Similarity	NPC471515
0.9355	High Similarity	NPC470402
0.9355	High Similarity	NPC476981
0.9355	High Similarity	NPC474836
0.9355	High Similarity	NPC156057
0.9355	High Similarity	NPC474208
0.9355	High Similarity	NPC162869
0.9355	High Similarity	NPC67876
0.9355	High Similarity	NPC78225
0.9351	High Similarity	NPC37392
0.9351	High Similarity	NPC256925
0.9351	High Similarity	NPC117992
0.9351	High Similarity	NPC168247
0.9351	High Similarity	NPC304745
0.9351	High Similarity	NPC200246
0.9351	High Similarity	NPC111341
0.9351	High Similarity	NPC472280
0.9351	High Similarity	NPC470681
0.9351	High Similarity	NPC152951
0.9351	High Similarity	NPC477958
0.9351	High Similarity	NPC57674

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 NPC475784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	905
0.2-0.3	1758
0.3-0.4	2610
0.4-0.5	1824
0.5-0.6	997
0.6-0.7	503
0.7-0.8	144
0.8-0.85	33
0.85-0.9	14
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9539	High Similarity	NPD2393	Clinical (unspecified phase)
0.9474	High Similarity	NPD1934	Approved
0.9245	High Similarity	NPD6166	Phase 2
0.9245	High Similarity	NPD6168	Clinical (unspecified phase)
0.9245	High Similarity	NPD6167	Clinical (unspecified phase)
0.9216	High Similarity	NPD4380	Phase 2
0.9161	High Similarity	NPD2801	Approved
0.9074	High Similarity	NPD7054	Approved
0.9018	High Similarity	NPD7074	Phase 3
0.9018	High Similarity	NPD7472	Approved
0.8947	High Similarity	NPD1511	Approved
0.8896	High Similarity	NPD3818	Discontinued
0.8889	High Similarity	NPD4378	Clinical (unspecified phase)
0.8875	High Similarity	NPD5494	Approved
0.8868	High Similarity	NPD4381	Clinical (unspecified phase)
0.8861	High Similarity	NPD3817	Phase 2
0.8855	High Similarity	NPD7808	Phase 3
0.8848	High Similarity	NPD6797	Phase 2
0.8831	High Similarity	NPD1512	Approved
0.8805	High Similarity	NPD3882	Suspended
0.8795	High Similarity	NPD7251	Discontinued
0.875	High Similarity	NPD7075	Discontinued
0.8743	High Similarity	NPD4338	Clinical (unspecified phase)
0.8727	High Similarity	NPD7804	Clinical (unspecified phase)
0.8688	High Similarity	NPD4868	Clinical (unspecified phase)
0.8679	High Similarity	NPD7096	Clinical (unspecified phase)
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8645	High Similarity	NPD7410	Clinical (unspecified phase)
0.8625	High Similarity	NPD8443	Clinical (unspecified phase)
0.8618	High Similarity	NPD1549	Phase 2
0.8616	High Similarity	NPD6801	Discontinued
0.8614	High Similarity	NPD5844	Phase 1
0.8487	Intermediate Similarity	NPD2796	Approved
0.8476	Intermediate Similarity	NPD6959	Discontinued
0.8447	Intermediate Similarity	NPD7819	Suspended
0.8438	Intermediate Similarity	NPD7411	Suspended
0.8424	Intermediate Similarity	NPD6232	Discontinued
0.8421	Intermediate Similarity	NPD1510	Phase 2
0.8383	Intermediate Similarity	NPD7473	Discontinued
0.8353	Intermediate Similarity	NPD6559	Discontinued
0.8294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD5402	Approved
0.8228	Intermediate Similarity	NPD6799	Approved
0.8187	Intermediate Similarity	NPD5403	Approved
0.8158	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1240	Approved
0.8158	Intermediate Similarity	NPD1613	Approved
0.8144	Intermediate Similarity	NPD1247	Approved
0.8133	Intermediate Similarity	NPD919	Approved
0.811	Intermediate Similarity	NPD1465	Phase 2
0.8107	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5401	Approved
0.8052	Intermediate Similarity	NPD1607	Approved
0.8037	Intermediate Similarity	NPD6599	Discontinued
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.7961	Intermediate Similarity	NPD3027	Phase 3
0.7925	Intermediate Similarity	NPD3750	Approved
0.7922	Intermediate Similarity	NPD943	Approved
0.7911	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7895	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2800	Approved
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3749	Approved
0.784	Intermediate Similarity	NPD2533	Approved
0.784	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD2534	Approved
0.7836	Intermediate Similarity	NPD3926	Phase 2
0.7833	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4628	Phase 3
0.7803	Intermediate Similarity	NPD3751	Discontinued
0.7784	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3787	Discontinued
0.7747	Intermediate Similarity	NPD4363	Phase 3
0.7747	Intermediate Similarity	NPD4360	Phase 2
0.7744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD920	Approved
0.773	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD1653	Approved
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7673	Intermediate Similarity	NPD6100	Approved
0.7673	Intermediate Similarity	NPD6099	Approved
0.7672	Intermediate Similarity	NPD7584	Approved
0.7663	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD447	Suspended
0.7643	Intermediate Similarity	NPD5124	Phase 1
0.7643	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD230	Phase 1
0.764	Intermediate Similarity	NPD8312	Approved
0.764	Intermediate Similarity	NPD8313	Approved
0.764	Intermediate Similarity	NPD1243	Approved
0.7627	Intermediate Similarity	NPD7685	Pre-registration
0.7622	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD37	Approved
0.761	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD7033	Discontinued
0.7607	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD7228	Approved
0.7595	Intermediate Similarity	NPD6651	Approved
0.7593	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD4965	Approved
0.7588	Intermediate Similarity	NPD4966	Approved
0.7588	Intermediate Similarity	NPD4967	Phase 2
0.7571	Intermediate Similarity	NPD5953	Discontinued
0.7564	Intermediate Similarity	NPD2313	Discontinued
0.7561	Intermediate Similarity	NPD7390	Discontinued
0.7561	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7286	Phase 2
0.7548	Intermediate Similarity	NPD4908	Phase 1
0.7546	Intermediate Similarity	NPD6190	Approved
0.7545	Intermediate Similarity	NPD3226	Approved
0.754	Intermediate Similarity	NPD6782	Approved
0.754	Intermediate Similarity	NPD6777	Approved
0.754	Intermediate Similarity	NPD6780	Approved
0.754	Intermediate Similarity	NPD6781	Approved
0.754	Intermediate Similarity	NPD6776	Approved
0.754	Intermediate Similarity	NPD6779	Approved
0.754	Intermediate Similarity	NPD6778	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7515	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2424	Discontinued
0.744	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7435	Discontinued
0.7418	Intermediate Similarity	NPD8434	Phase 2
0.7412	Intermediate Similarity	NPD6844	Discontinued
0.7409	Intermediate Similarity	NPD8151	Discontinued
0.7407	Intermediate Similarity	NPD2344	Approved
0.7391	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4625	Phase 3
0.7372	Intermediate Similarity	NPD9494	Approved
0.7371	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD5711	Approved
0.7368	Intermediate Similarity	NPD8455	Phase 2
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7783	Phase 2
0.733	Intermediate Similarity	NPD7698	Approved
0.733	Intermediate Similarity	NPD7696	Phase 3
0.733	Intermediate Similarity	NPD7697	Approved
0.7326	Intermediate Similarity	NPD4361	Phase 2
0.7326	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1610	Phase 2
0.7317	Intermediate Similarity	NPD1652	Phase 2
0.7305	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7871	Phase 2
0.7292	Intermediate Similarity	NPD7870	Phase 2
0.7285	Intermediate Similarity	NPD1548	Phase 1
0.7278	Intermediate Similarity	NPD3823	Discontinued
0.7277	Intermediate Similarity	NPD6823	Phase 2
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7268	Intermediate Similarity	NPD7701	Phase 2
0.7268	Intermediate Similarity	NPD7585	Approved
0.7244	Intermediate Similarity	NPD1203	Approved
0.7238	Intermediate Similarity	NPD7240	Approved
0.7235	Intermediate Similarity	NPD7458	Discontinued
0.7233	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6798	Discontinued
0.7232	Intermediate Similarity	NPD5242	Approved
0.7229	Intermediate Similarity	NPD2309	Approved
0.7225	Intermediate Similarity	NPD5353	Approved
0.7216	Intermediate Similarity	NPD8127	Discontinued
0.7216	Intermediate Similarity	NPD7583	Approved
0.7215	Intermediate Similarity	NPD6832	Phase 2
0.7212	Intermediate Similarity	NPD6674	Discontinued
0.7212	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7549	Discontinued
0.7197	Intermediate Similarity	NPD2798	Approved
0.7195	Intermediate Similarity	NPD7266	Discontinued
0.7194	Intermediate Similarity	NPD7874	Approved
0.7194	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4308	Phase 3
0.7175	Intermediate Similarity	NPD7229	Phase 3
0.7158	Intermediate Similarity	NPD7699	Phase 2
0.7158	Intermediate Similarity	NPD7700	Phase 2
0.7157	Intermediate Similarity	NPD7801	Approved
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7134	Intermediate Similarity	NPD2797	Approved
0.7115	Intermediate Similarity	NPD4749	Approved
0.7101	Intermediate Similarity	NPD4662	Approved
0.7101	Intermediate Similarity	NPD4661	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