NPASS Compound

Structure

NPC473990 OpenBabel07101718222D 28 31 0 0 1 0 0 0 0 0999 V2000 -1.1248 -0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 1.1088 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 2.0000 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 0.0000 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 2.5981 1.5000 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 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 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 -0.8660 0.5000 0.0000 C 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 21 1 0 0 0 0 3 26 1 0 0 0 0 4 10 2 0 0 0 0 4 11 1 0 0 0 0 5 10 1 0 0 0 0 5 17 2 0 0 0 0 6 11 1 0 0 0 0 6 18 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 11 20 2 0 0 0 0 12 22 1 0 0 0 0 13 19 2 0 0 0 0 13 23 1 0 0 0 0 14 19 1 0 0 0 0 14 24 2 0 0 0 0 15 10 1 6 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 21 1 0 0 0 0 18 25 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:	386.14
Volume:	380.623
LogP:	3.368
LogD:	2.913
LogS:	-4.039
# Rotatable Bonds:	2
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.729
Synthetic Accessibility Score:	3.689
Fsp3:	0.381
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:	-4.848
MDCK Permeability:	1.2792854249710217e-05
Pgp-inhibitor:	0.032
Pgp-substrate:	0.459
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	92.14652252197266%
Volume Distribution (VD):	1.027
Pgp-substrate:	8.021285057067871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.19
CYP1A2-substrate:	0.387
CYP2C19-inhibitor:	0.356
CYP2C19-substrate:	0.19
CYP2C9-inhibitor:	0.694
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.593
CYP2D6-substrate:	0.318
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.322

ADMET: Excretion

Clearance (CL):	13.419
Half-life (T1/2):	0.393

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.566
Drug-inuced Liver Injury (DILI):	0.683
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.865
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.845
Carcinogencity:	0.499
Eye Corrosion:	0.003
Eye Irritation:	0.07
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC473990

Natural Product ID:	NPC473990
*Common Name:**	(2S)-3',5,7-Trihydroxy-8'-Methoxy-2',2'-Dimethyl-2,6'-Bichroman-4-One
IUPAC Name:	(2S)-5,7-dihydroxy-2-(3-hydroxy-8-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	HTNJCCKJJVLCTO-BUSXIPJBSA-N
Standard InCHI:	InChI=1S/C21H22O7/c1-21(2)18(25)6-11-4-10(5-17(26-3)20(11)28-21)15-9-14(24)19-13(23)7-12(22)8-16(19)27-15/h4-5,7-8,15,18,22-23,25H,6,9H2,1-3H3/t15-,18?/m0/s1
SMILES:	CC1(C(CC2=C(O1)C(=CC(=C2)C3CC(=O)C4=C(C=C(C=C4O3)O)O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457525
PubChem CID:	25147601
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003643] 3'-prenylated flavans [CHEMONTID:0003506] 3'-prenylated flavanones

*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	=	18200.0	nM	PMID[569967]

☑ 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 NPC473990 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	397
0.1-0.2	1610
0.2-0.3	3906
0.3-0.4	9585
0.4-0.5	8793
0.5-0.6	3453
0.6-0.7	4743
0.7-0.8	5468
0.8-0.85	2956
0.85-0.9	1395
0.9-0.95	329
0.95-1	62

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC174953
0.9868	High Similarity	NPC472632
0.9804	High Similarity	NPC474033
0.9804	High Similarity	NPC474034
0.9803	High Similarity	NPC475784
0.9739	High Similarity	NPC474038
0.9739	High Similarity	NPC134783
0.9739	High Similarity	NPC471211
0.9739	High Similarity	NPC471210
0.9739	High Similarity	NPC471212
0.9673	High Similarity	NPC119209
0.9673	High Similarity	NPC472631
0.9673	High Similarity	NPC192686
0.9673	High Similarity	NPC118256
0.9673	High Similarity	NPC472630
0.9671	High Similarity	NPC27337
0.9671	High Similarity	NPC472598
0.9671	High Similarity	NPC473272
0.9671	High Similarity	NPC474055
0.9671	High Similarity	NPC284820
0.9671	High Similarity	NPC471209
0.9669	High Similarity	NPC45849
0.9669	High Similarity	NPC200761
0.9669	High Similarity	NPC470327
0.9669	High Similarity	NPC477503
0.9615	High Similarity	NPC471213
0.9613	High Similarity	NPC472625
0.961	High Similarity	NPC472634
0.961	High Similarity	NPC26326
0.9605	High Similarity	NPC209614
0.9605	High Similarity	NPC195796
0.9605	High Similarity	NPC470328
0.9605	High Similarity	NPC291878
0.9605	High Similarity	NPC472626
0.9605	High Similarity	NPC278778
0.9605	High Similarity	NPC35038
0.9603	High Similarity	NPC74924
0.96	High Similarity	NPC474021
0.96	High Similarity	NPC474023
0.9554	High Similarity	NPC6588
0.9554	High Similarity	NPC477154
0.9554	High Similarity	NPC117854
0.9554	High Similarity	NPC474024
0.9551	High Similarity	NPC62261
0.9551	High Similarity	NPC293319
0.9548	High Similarity	NPC476247
0.9548	High Similarity	NPC472635
0.9545	High Similarity	NPC470326
0.9545	High Similarity	NPC472624
0.9545	High Similarity	NPC287328
0.9545	High Similarity	NPC282009
0.9542	High Similarity	NPC52889
0.9542	High Similarity	NPC223787
0.9542	High Similarity	NPC291508
0.9539	High Similarity	NPC321779
0.9539	High Similarity	NPC226025
0.9536	High Similarity	NPC106976
0.9536	High Similarity	NPC475790
0.9533	High Similarity	NPC338131
0.9487	High Similarity	NPC124038
0.9487	High Similarity	NPC186686
0.9484	High Similarity	NPC471499
0.9484	High Similarity	NPC142252
0.9481	High Similarity	NPC53545
0.9481	High Similarity	NPC117418
0.9481	High Similarity	NPC22192
0.9474	High Similarity	NPC192083
0.9474	High Similarity	NPC298692
0.9474	High Similarity	NPC18727
0.9474	High Similarity	NPC213896
0.943	High Similarity	NPC477502
0.9423	High Similarity	NPC220912
0.9423	High Similarity	NPC474162
0.9423	High Similarity	NPC474150
0.9419	High Similarity	NPC471976
0.9419	High Similarity	NPC36217
0.9416	High Similarity	NPC78071
0.9412	High Similarity	NPC477958
0.9408	High Similarity	NPC219582
0.9408	High Similarity	NPC302950
0.9408	High Similarity	NPC236637
0.9408	High Similarity	NPC471982
0.9371	High Similarity	NPC326877
0.9367	High Similarity	NPC119589
0.9367	High Similarity	NPC120593
0.9367	High Similarity	NPC43319
0.9363	High Similarity	NPC236521
0.9363	High Similarity	NPC152659
0.9363	High Similarity	NPC273959
0.9363	High Similarity	NPC474240
0.9363	High Similarity	NPC248638
0.9359	High Similarity	NPC228383
0.9359	High Similarity	NPC173137
0.9359	High Similarity	NPC289771
0.9359	High Similarity	NPC3629
0.9359	High Similarity	NPC158188
0.9355	High Similarity	NPC204879
0.9355	High Similarity	NPC184755
0.9355	High Similarity	NPC250214
0.9355	High Similarity	NPC74178
0.9355	High Similarity	NPC95936
0.9355	High Similarity	NPC187792
0.9351	High Similarity	NPC326037
0.9351	High Similarity	NPC208152
0.9351	High Similarity	NPC78492
0.9351	High Similarity	NPC471985
0.9351	High Similarity	NPC320825
0.9351	High Similarity	NPC470600
0.9351	High Similarity	NPC13858
0.9351	High Similarity	NPC250922
0.9346	High Similarity	NPC472583
0.9346	High Similarity	NPC469405
0.9346	High Similarity	NPC223701
0.9346	High Similarity	NPC7989
0.9342	High Similarity	NPC472422
0.9342	High Similarity	NPC472420
0.9342	High Similarity	NPC471676
0.9342	High Similarity	NPC244577
0.9342	High Similarity	NPC263384
0.9342	High Similarity	NPC471677
0.9313	High Similarity	NPC103307
0.9308	High Similarity	NPC218226
0.9304	High Similarity	NPC300053
0.9304	High Similarity	NPC36
0.9304	High Similarity	NPC108433
0.9304	High Similarity	NPC234052
0.9304	High Similarity	NPC475888
0.9304	High Similarity	NPC7688
0.9304	High Similarity	NPC125039
0.9304	High Similarity	NPC58223
0.9304	High Similarity	NPC72787
0.9304	High Similarity	NPC224280
0.9304	High Similarity	NPC7154
0.9304	High Similarity	NPC36916
0.9299	High Similarity	NPC472964
0.9299	High Similarity	NPC201800
0.9299	High Similarity	NPC211107
0.9299	High Similarity	NPC83922
0.9299	High Similarity	NPC25152
0.9299	High Similarity	NPC472448
0.9295	High Similarity	NPC204290
0.9295	High Similarity	NPC470183
0.9295	High Similarity	NPC328102
0.9295	High Similarity	NPC472902
0.9295	High Similarity	NPC299436
0.9295	High Similarity	NPC101731
0.9295	High Similarity	NPC321399
0.929	High Similarity	NPC471479
0.929	High Similarity	NPC471515
0.929	High Similarity	NPC475267
0.929	High Similarity	NPC474208
0.929	High Similarity	NPC162869
0.929	High Similarity	NPC156057
0.929	High Similarity	NPC474836
0.929	High Similarity	NPC67876
0.929	High Similarity	NPC262286
0.929	High Similarity	NPC78225
0.929	High Similarity	NPC63454
0.929	High Similarity	NPC218313
0.929	High Similarity	NPC52530
0.929	High Similarity	NPC36852
0.929	High Similarity	NPC48208
0.929	High Similarity	NPC474681
0.929	High Similarity	NPC183851
0.9286	High Similarity	NPC48579
0.9286	High Similarity	NPC304207
0.9286	High Similarity	NPC152951
0.9286	High Similarity	NPC117992
0.9286	High Similarity	NPC217706
0.9286	High Similarity	NPC168247
0.9286	High Similarity	NPC207809
0.9286	High Similarity	NPC37392
0.9286	High Similarity	NPC256925
0.9286	High Similarity	NPC57674
0.9286	High Similarity	NPC259710
0.9286	High Similarity	NPC234255
0.9286	High Similarity	NPC230149
0.9281	High Similarity	NPC161881
0.9281	High Similarity	NPC56232
0.9281	High Similarity	NPC40033
0.9281	High Similarity	NPC150123
0.9281	High Similarity	NPC244583
0.9281	High Similarity	NPC472912
0.9281	High Similarity	NPC10807
0.9276	High Similarity	NPC472633
0.9272	High Similarity	NPC476342
0.9267	High Similarity	NPC24136
0.9267	High Similarity	NPC187282
0.9267	High Similarity	NPC290133
0.9255	High Similarity	NPC121333
0.9255	High Similarity	NPC256760
0.925	High Similarity	NPC152477
0.925	High Similarity	NPC288813
0.925	High Similarity	NPC475212
0.925	High Similarity	NPC177480
0.9245	High Similarity	NPC207575
0.9245	High Similarity	NPC13481
0.9245	High Similarity	NPC173292
0.9245	High Similarity	NPC272502
0.9245	High Similarity	NPC5778

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 NPC473990 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	927
0.2-0.3	1832
0.3-0.4	2603
0.4-0.5	1791
0.5-0.6	988
0.6-0.7	461
0.7-0.8	143
0.8-0.85	31
0.85-0.9	12
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9474	High Similarity	NPD2393	Clinical (unspecified phase)
0.9408	High Similarity	NPD1934	Approved
0.9304	High Similarity	NPD6167	Clinical (unspecified phase)
0.9304	High Similarity	NPD6166	Phase 2
0.9304	High Similarity	NPD6168	Clinical (unspecified phase)
0.9074	High Similarity	NPD7074	Phase 3
0.9026	High Similarity	NPD4380	Phase 2
0.9012	High Similarity	NPD7054	Approved
0.8974	High Similarity	NPD2801	Approved
0.8957	High Similarity	NPD7472	Approved
0.8931	High Similarity	NPD5494	Approved
0.8795	High Similarity	NPD7808	Phase 3
0.8788	High Similarity	NPD6797	Phase 2
0.8758	High Similarity	NPD1511	Approved
0.8742	High Similarity	NPD3882	Suspended
0.8742	High Similarity	NPD4868	Clinical (unspecified phase)
0.8735	High Similarity	NPD7251	Discontinued
0.872	High Similarity	NPD3818	Discontinued
0.8701	High Similarity	NPD4378	Clinical (unspecified phase)
0.8688	High Similarity	NPD7075	Discontinued
0.8688	High Similarity	NPD4381	Clinical (unspecified phase)
0.8679	High Similarity	NPD3817	Phase 2
0.8667	High Similarity	NPD7804	Clinical (unspecified phase)
0.8645	High Similarity	NPD1512	Approved
0.8642	High Similarity	NPD6959	Discontinued
0.8616	High Similarity	NPD7096	Clinical (unspecified phase)
0.8609	High Similarity	NPD1552	Clinical (unspecified phase)
0.8609	High Similarity	NPD1550	Clinical (unspecified phase)
0.8571	High Similarity	NPD4338	Clinical (unspecified phase)
0.8562	High Similarity	NPD8443	Clinical (unspecified phase)
0.8554	High Similarity	NPD5844	Phase 1
0.8553	High Similarity	NPD1549	Phase 2
0.8462	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD6801	Discontinued
0.8385	Intermediate Similarity	NPD7819	Suspended
0.8375	Intermediate Similarity	NPD7411	Suspended
0.8364	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8301	Intermediate Similarity	NPD2796	Approved
0.8294	Intermediate Similarity	NPD6559	Discontinued
0.8272	Intermediate Similarity	NPD1465	Phase 2
0.8235	Intermediate Similarity	NPD1510	Phase 2
0.8165	Intermediate Similarity	NPD6799	Approved
0.811	Intermediate Similarity	NPD5402	Approved
0.8092	Intermediate Similarity	NPD1613	Approved
0.8092	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1240	Approved
0.8047	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5403	Approved
0.7987	Intermediate Similarity	NPD1607	Approved
0.7976	Intermediate Similarity	NPD1247	Approved
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7964	Intermediate Similarity	NPD919	Approved
0.7952	Intermediate Similarity	NPD7768	Phase 2
0.7911	Intermediate Similarity	NPD2800	Approved
0.7895	Intermediate Similarity	NPD3027	Phase 3
0.7888	Intermediate Similarity	NPD2532	Approved
0.7888	Intermediate Similarity	NPD5401	Approved
0.7888	Intermediate Similarity	NPD2534	Approved
0.7888	Intermediate Similarity	NPD2533	Approved
0.7881	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD943	Approved
0.7848	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2935	Discontinued
0.7829	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD3749	Approved
0.7778	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3926	Phase 2
0.775	Intermediate Similarity	NPD4628	Phase 3
0.775	Intermediate Similarity	NPD3750	Approved
0.7746	Intermediate Similarity	NPD7228	Approved
0.7746	Intermediate Similarity	NPD3751	Discontinued
0.7722	Intermediate Similarity	NPD6100	Approved
0.7722	Intermediate Similarity	NPD6099	Approved
0.7719	Intermediate Similarity	NPD3787	Discontinued
0.7692	Intermediate Similarity	NPD230	Phase 1
0.7684	Intermediate Similarity	NPD8313	Approved
0.7684	Intermediate Similarity	NPD8312	Approved
0.7683	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD37	Approved
0.7661	Intermediate Similarity	NPD7199	Phase 2
0.7647	Intermediate Similarity	NPD6234	Discontinued
0.7643	Intermediate Similarity	NPD6651	Approved
0.7633	Intermediate Similarity	NPD4966	Approved
0.7633	Intermediate Similarity	NPD4965	Approved
0.7633	Intermediate Similarity	NPD4967	Phase 2
0.7627	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1551	Phase 2
0.7607	Intermediate Similarity	NPD7390	Discontinued
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD4360	Phase 2
0.7596	Intermediate Similarity	NPD4363	Phase 3
0.758	Intermediate Similarity	NPD447	Suspended
0.7578	Intermediate Similarity	NPD1243	Approved
0.7576	Intermediate Similarity	NPD920	Approved
0.7547	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD8151	Discontinued
0.7531	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1653	Approved
0.7526	Intermediate Similarity	NPD7584	Approved
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.7514	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7485	Intermediate Similarity	NPD6190	Approved
0.7485	Intermediate Similarity	NPD3226	Approved
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.7472	Intermediate Similarity	NPD7685	Pre-registration
0.7471	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1933	Approved
0.7468	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5124	Phase 1
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7455	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2346	Discontinued
0.7439	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2799	Discontinued
0.7438	Intermediate Similarity	NPD7033	Discontinued
0.7438	Intermediate Similarity	NPD3748	Approved
0.7423	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5711	Approved
0.7414	Intermediate Similarity	NPD5710	Approved
0.7412	Intermediate Similarity	NPD8455	Phase 2
0.7407	Intermediate Similarity	NPD2424	Discontinued
0.7389	Intermediate Similarity	NPD2313	Discontinued
0.7381	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7240	Approved
0.7371	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7783	Phase 2
0.7368	Intermediate Similarity	NPD7698	Approved
0.7368	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7435	Discontinued
0.7368	Intermediate Similarity	NPD7697	Approved
0.7368	Intermediate Similarity	NPD7696	Phase 3
0.7363	Intermediate Similarity	NPD8434	Phase 2
0.7349	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2344	Approved
0.7329	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4625	Phase 3
0.7308	Intermediate Similarity	NPD9494	Approved
0.7306	Intermediate Similarity	NPD7701	Phase 2
0.7294	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5353	Approved
0.7256	Intermediate Similarity	NPD6674	Discontinued
0.7255	Intermediate Similarity	NPD1610	Phase 2
0.7251	Intermediate Similarity	NPD6844	Discontinued
0.724	Intermediate Similarity	NPD7870	Phase 2
0.724	Intermediate Similarity	NPD7871	Phase 2
0.7239	Intermediate Similarity	NPD7266	Discontinued
0.7225	Intermediate Similarity	NPD6823	Phase 2
0.7222	Intermediate Similarity	NPD3823	Discontinued
0.7219	Intermediate Similarity	NPD6535	Approved
0.7219	Intermediate Similarity	NPD6534	Approved
0.7196	Intermediate Similarity	NPD7700	Phase 2
0.7196	Intermediate Similarity	NPD7699	Phase 2
0.7181	Intermediate Similarity	NPD4361	Phase 2
0.7181	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1203	Approved
0.7176	Intermediate Similarity	NPD7458	Discontinued
0.7175	Intermediate Similarity	NPD5242	Approved
0.717	Intermediate Similarity	NPD6798	Discontinued
0.7169	Intermediate Similarity	NPD2309	Approved
0.7161	Intermediate Similarity	NPD4749	Approved
0.7159	Intermediate Similarity	NPD8127	Discontinued
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7152	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7874	Approved
0.7135	Intermediate Similarity	NPD2403	Approved
0.7128	Intermediate Similarity	NPD7585	Approved
0.7119	Intermediate Similarity	NPD7229	Phase 3
0.7107	Intermediate Similarity	NPD7801	Approved
0.7105	Intermediate Similarity	NPD1548	Phase 1
0.7089	Intermediate Similarity	NPD2861	Phase 2
0.7081	Intermediate Similarity	NPD4060	Phase 1
0.7077	Intermediate Similarity	NPD7583	Approved
0.7063	Intermediate Similarity	NPD3268	Approved
0.7062	Intermediate Similarity	NPD8320	Phase 1
0.7062	Intermediate Similarity	NPD8319	Approved
0.7049	Intermediate Similarity	NPD7549	Discontinued
0.7048	Intermediate Similarity	NPD2654	Approved
0.7041	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