NPASS Compound

Structure

NPC186686 OpenBabel07101718282D 31 34 0 0 1 0 0 0 0 0999 V2000 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 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 0.8660 -1.5000 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 6.0622 -3.5000 0.0000 C 0 0 0 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 3.4641 -2.0000 0.0000 C 0 0 1 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 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 5.1962 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 3.4641 -3.0000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 13 2 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 25 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 22 2 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 14 26 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 24 1 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 28 2 0 0 0 0 20 24 2 0 0 0 0 20 29 1 0 0 0 0 21 17 1 6 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 0 0 0 0 24 31 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.17
Volume:	435.743
LogP:	5.93
LogD:	4.298
LogS:	-3.167
# Rotatable Bonds:	3
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	3.846
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.836
MDCK Permeability:	1.7502907212474383e-05
Pgp-inhibitor:	0.166
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.604
30% Bioavailability (F30%):	0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	98.06594848632812%
Volume Distribution (VD):	0.774
Pgp-substrate:	3.0476303100585938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.694
CYP1A2-substrate:	0.447
CYP2C19-inhibitor:	0.919
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.913
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.94
CYP2D6-substrate:	0.336
CYP3A4-inhibitor:	0.751
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	13.528
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.226
Human Hepatotoxicity (H-HT):	0.889
Drug-inuced Liver Injury (DILI):	0.888
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.891
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.899
Carcinogencity:	0.785
Eye Corrosion:	0.003
Eye Irritation:	0.286
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC186686

Natural Product ID:	NPC186686
*Common Name:**	(S)-5,7,8'-Trihydroxy-2',2'-Dimethyl-5'-(3-Methylbut-2-Enyl)-2,6'-Bichroman-4-One
IUPAC Name:	(2S)-5,7-dihydroxy-2-[8-hydroxy-2,2-dimethyl-5-(3-methylbut-2-enyl)chromen-6-yl]-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	DOHUWPORVBGXGM-NRFANRHFSA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-13(2)5-6-15-16-7-8-25(3,4)31-24(16)20(29)11-17(15)21-12-19(28)23-18(27)9-14(26)10-22(23)30-21/h5,7-11,21,26-27,29H,6,12H2,1-4H3/t21-/m0/s1
SMILES:	CC(=CCc1c2C=CC(C)(C)Oc2c(cc1[C@@H]1CC(=O)c2c(cc(cc2O1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458936
PubChem CID:	44589106
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003645] 2'-prenylated flavans [CHEMONTID:0003588] 2'-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	=	13900.0	nM	PMID[491585]

☑ 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 NPC186686 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	419
0.1-0.2	1646
0.2-0.3	3851
0.3-0.4	9756
0.4-0.5	8558
0.5-0.6	3231
0.6-0.7	4812
0.7-0.8	5601
0.8-0.85	2991
0.85-0.9	1464
0.9-0.95	323
0.95-1	45

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC43319
0.9809	High Similarity	NPC218226
0.9808	High Similarity	NPC293319
0.9805	High Similarity	NPC118256
0.9805	High Similarity	NPC192686
0.9805	High Similarity	NPC36217
0.9805	High Similarity	NPC119209
0.9742	High Similarity	NPC474038
0.9682	High Similarity	NPC472450
0.9682	High Similarity	NPC275780
0.9682	High Similarity	NPC239752
0.9679	High Similarity	NPC474150
0.9679	High Similarity	NPC201800
0.9679	High Similarity	NPC474162
0.9677	High Similarity	NPC471973
0.9677	High Similarity	NPC474960
0.9677	High Similarity	NPC475784
0.9675	High Similarity	NPC27337
0.9675	High Similarity	NPC284820
0.9675	High Similarity	NPC473272
0.962	High Similarity	NPC272502
0.962	High Similarity	NPC39091
0.9618	High Similarity	NPC23298
0.9618	High Similarity	NPC189473
0.9618	High Similarity	NPC472625
0.9615	High Similarity	NPC471210
0.9615	High Similarity	NPC26326
0.9615	High Similarity	NPC472632
0.9613	High Similarity	NPC210459
0.961	High Similarity	NPC278778
0.961	High Similarity	NPC291878
0.961	High Similarity	NPC24640
0.961	High Similarity	NPC195796
0.961	High Similarity	NPC35038
0.956	High Similarity	NPC477154
0.956	High Similarity	NPC117854
0.956	High Similarity	NPC474024
0.956	High Similarity	NPC6588
0.9557	High Similarity	NPC303174
0.9557	High Similarity	NPC62261
0.9554	High Similarity	NPC472964
0.9554	High Similarity	NPC474033
0.9554	High Similarity	NPC474034
0.9554	High Similarity	NPC229632
0.9551	High Similarity	NPC472624
0.9551	High Similarity	NPC299436
0.9551	High Similarity	NPC472902
0.9551	High Similarity	NPC174953
0.9551	High Similarity	NPC321399
0.9548	High Similarity	NPC474055
0.9548	High Similarity	NPC52889
0.9548	High Similarity	NPC136674
0.9548	High Similarity	NPC471209
0.9548	High Similarity	NPC291508
0.9548	High Similarity	NPC472598
0.9545	High Similarity	NPC67396
0.9545	High Similarity	NPC45849
0.9545	High Similarity	NPC200761
0.9545	High Similarity	NPC470327
0.9545	High Similarity	NPC477503
0.95	High Similarity	NPC288813
0.9497	High Similarity	NPC170245
0.9497	High Similarity	NPC472449
0.9497	High Similarity	NPC37870
0.9494	High Similarity	NPC236521
0.9494	High Similarity	NPC152659
0.9494	High Similarity	NPC248638
0.949	High Similarity	NPC134783
0.949	High Similarity	NPC471211
0.949	High Similarity	NPC471212
0.949	High Similarity	NPC472634
0.949	High Similarity	NPC61010
0.9487	High Similarity	NPC85121
0.9487	High Similarity	NPC74178
0.9487	High Similarity	NPC53545
0.9487	High Similarity	NPC204879
0.9487	High Similarity	NPC117418
0.9487	High Similarity	NPC473990
0.9487	High Similarity	NPC184755
0.9484	High Similarity	NPC471985
0.9484	High Similarity	NPC209614
0.9484	High Similarity	NPC470328
0.9484	High Similarity	NPC472626
0.9481	High Similarity	NPC18727
0.9481	High Similarity	NPC192083
0.9481	High Similarity	NPC213896
0.9481	High Similarity	NPC74924
0.9437	High Similarity	NPC150131
0.9434	High Similarity	NPC326520
0.9434	High Similarity	NPC475888
0.943	High Similarity	NPC211107
0.943	High Similarity	NPC83922
0.943	High Similarity	NPC329760
0.943	High Similarity	NPC472448
0.943	High Similarity	NPC472635
0.943	High Similarity	NPC476247
0.943	High Similarity	NPC25152
0.9427	High Similarity	NPC14353
0.9427	High Similarity	NPC287328
0.9427	High Similarity	NPC472630
0.9427	High Similarity	NPC56085
0.9427	High Similarity	NPC139036
0.9427	High Similarity	NPC204290
0.9427	High Similarity	NPC472631
0.9427	High Similarity	NPC328102
0.9427	High Similarity	NPC282009
0.9427	High Similarity	NPC228785
0.9423	High Similarity	NPC218313
0.9423	High Similarity	NPC223787
0.9423	High Similarity	NPC474681
0.9423	High Similarity	NPC472963
0.9419	High Similarity	NPC234255
0.9419	High Similarity	NPC321779
0.9419	High Similarity	NPC226025
0.9416	High Similarity	NPC471982
0.9416	High Similarity	NPC106976
0.9416	High Similarity	NPC302950
0.9416	High Similarity	NPC219582
0.9416	High Similarity	NPC236637
0.9383	High Similarity	NPC4200
0.9379	High Similarity	NPC165456
0.9375	High Similarity	NPC120593
0.9375	High Similarity	NPC471213
0.9375	High Similarity	NPC477517
0.9371	High Similarity	NPC12461
0.9371	High Similarity	NPC124038
0.9371	High Similarity	NPC474240
0.9371	High Similarity	NPC207690
0.9371	High Similarity	NPC220313
0.9371	High Similarity	NPC7483
0.9371	High Similarity	NPC476295
0.9371	High Similarity	NPC475985
0.9367	High Similarity	NPC173137
0.9367	High Similarity	NPC289771
0.9367	High Similarity	NPC142252
0.9367	High Similarity	NPC278052
0.9367	High Similarity	NPC57715
0.9367	High Similarity	NPC29876
0.9367	High Similarity	NPC474186
0.9367	High Similarity	NPC234644
0.9367	High Similarity	NPC167678
0.9367	High Similarity	NPC40491
0.9367	High Similarity	NPC474187
0.9367	High Similarity	NPC471499
0.9363	High Similarity	NPC280680
0.9363	High Similarity	NPC95936
0.9363	High Similarity	NPC100123
0.9363	High Similarity	NPC250214
0.9363	High Similarity	NPC22192
0.9363	High Similarity	NPC474290
0.9363	High Similarity	NPC235448
0.9363	High Similarity	NPC476242
0.9359	High Similarity	NPC472907
0.9359	High Similarity	NPC133970
0.9359	High Similarity	NPC6633
0.9359	High Similarity	NPC5322
0.9359	High Similarity	NPC282307
0.9359	High Similarity	NPC472455
0.9359	High Similarity	NPC170026
0.9355	High Similarity	NPC472905
0.9355	High Similarity	NPC298692
0.9355	High Similarity	NPC170492
0.9321	High Similarity	NPC472276
0.9317	High Similarity	NPC476306
0.9313	High Similarity	NPC224280
0.9313	High Similarity	NPC472277
0.9313	High Similarity	NPC108433
0.9313	High Similarity	NPC300053
0.9308	High Similarity	NPC472402
0.9308	High Similarity	NPC78332
0.9308	High Similarity	NPC194427
0.9308	High Similarity	NPC261470
0.9308	High Similarity	NPC206605
0.9304	High Similarity	NPC188433
0.9304	High Similarity	NPC297212
0.9304	High Similarity	NPC320359
0.9304	High Similarity	NPC470183
0.9304	High Similarity	NPC200746
0.9304	High Similarity	NPC475886
0.9304	High Similarity	NPC476980
0.9304	High Similarity	NPC476280
0.9304	High Similarity	NPC470326
0.9304	High Similarity	NPC474287
0.9304	High Similarity	NPC476283
0.9299	High Similarity	NPC471479
0.9299	High Similarity	NPC474836
0.9299	High Similarity	NPC475267
0.9299	High Similarity	NPC299520
0.9299	High Similarity	NPC474208
0.9299	High Similarity	NPC48208
0.9299	High Similarity	NPC300727
0.9299	High Similarity	NPC471515
0.9299	High Similarity	NPC273843
0.9299	High Similarity	NPC78071
0.9299	High Similarity	NPC67876
0.9299	High Similarity	NPC129684
0.9299	High Similarity	NPC165977
0.9299	High Similarity	NPC156057
0.9299	High Similarity	NPC241904
0.9299	High Similarity	NPC78225

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 NPC186686 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	937
0.2-0.3	1730
0.3-0.4	2634
0.4-0.5	1809
0.5-0.6	981
0.6-0.7	484
0.7-0.8	151
0.8-0.85	34
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9481	High Similarity	NPD2393	Clinical (unspecified phase)
0.9416	High Similarity	NPD1934	Approved
0.9108	High Similarity	NPD2801	Approved
0.9074	High Similarity	NPD6167	Clinical (unspecified phase)
0.9074	High Similarity	NPD6168	Clinical (unspecified phase)
0.9074	High Similarity	NPD6166	Phase 2
0.8917	High Similarity	NPD4380	Phase 2
0.8909	High Similarity	NPD7054	Approved
0.8896	High Similarity	NPD1511	Approved
0.8855	High Similarity	NPD7074	Phase 3
0.8855	High Similarity	NPD7472	Approved
0.8827	High Similarity	NPD5494	Approved
0.8782	High Similarity	NPD1512	Approved
0.8758	High Similarity	NPD3882	Suspended
0.8735	High Similarity	NPD3818	Discontinued
0.8718	High Similarity	NPD4378	Clinical (unspecified phase)
0.8696	High Similarity	NPD3817	Phase 2
0.869	High Similarity	NPD6797	Phase 2
0.8683	High Similarity	NPD5844	Phase 1
0.8659	High Similarity	NPD6959	Discontinued
0.8642	High Similarity	NPD4868	Clinical (unspecified phase)
0.8639	High Similarity	NPD7251	Discontinued
0.8634	High Similarity	NPD7819	Suspended
0.8606	High Similarity	NPD6232	Discontinued
0.8589	High Similarity	NPD7075	Discontinued
0.8589	High Similarity	NPD4381	Clinical (unspecified phase)
0.8588	High Similarity	NPD4338	Clinical (unspecified phase)
0.8588	High Similarity	NPD7808	Phase 3
0.858	High Similarity	NPD8443	Clinical (unspecified phase)
0.8563	High Similarity	NPD7473	Discontinued
0.8519	High Similarity	NPD7096	Clinical (unspecified phase)
0.8506	High Similarity	NPD1550	Clinical (unspecified phase)
0.8506	High Similarity	NPD1552	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8405	Intermediate Similarity	NPD1465	Phase 2
0.8344	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD2796	Approved
0.8282	Intermediate Similarity	NPD7411	Suspended
0.8258	Intermediate Similarity	NPD1510	Phase 2
0.815	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD3750	Approved
0.8103	Intermediate Similarity	NPD6559	Discontinued
0.8101	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6799	Approved
0.807	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD3749	Approved
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8024	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD1613	Approved
0.7989	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD919	Approved
0.7976	Intermediate Similarity	NPD7768	Phase 2
0.7927	Intermediate Similarity	NPD5403	Approved
0.7901	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1607	Approved
0.7892	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD943	Approved
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.7874	Intermediate Similarity	NPD3751	Discontinued
0.7857	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD3787	Discontinued
0.7826	Intermediate Similarity	NPD2800	Approved
0.7821	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3027	Phase 3
0.7805	Intermediate Similarity	NPD5401	Approved
0.7803	Intermediate Similarity	NPD3926	Phase 2
0.7799	Intermediate Similarity	NPD3748	Approved
0.7792	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.7771	Intermediate Similarity	NPD7228	Approved
0.775	Intermediate Similarity	NPD2935	Discontinued
0.775	Intermediate Similarity	NPD6099	Approved
0.775	Intermediate Similarity	NPD6100	Approved
0.7744	Intermediate Similarity	NPD7390	Discontinued
0.7725	Intermediate Similarity	NPD3226	Approved
0.7716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD8313	Approved
0.7709	Intermediate Similarity	NPD8312	Approved
0.7702	Intermediate Similarity	NPD2346	Discontinued
0.7701	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4628	Phase 3
0.7661	Intermediate Similarity	NPD4966	Approved
0.7661	Intermediate Similarity	NPD4965	Approved
0.7661	Intermediate Similarity	NPD4967	Phase 2
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4360	Phase 2
0.7622	Intermediate Similarity	NPD4363	Phase 3
0.761	Intermediate Similarity	NPD230	Phase 1
0.7606	Intermediate Similarity	NPD6778	Approved
0.7606	Intermediate Similarity	NPD6777	Approved
0.7606	Intermediate Similarity	NPD6779	Approved
0.7606	Intermediate Similarity	NPD6776	Approved
0.7606	Intermediate Similarity	NPD6782	Approved
0.7606	Intermediate Similarity	NPD6780	Approved
0.7606	Intermediate Similarity	NPD6781	Approved
0.7605	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD920	Approved
0.7598	Intermediate Similarity	NPD7685	Pre-registration
0.759	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8150	Discontinued
0.758	Intermediate Similarity	NPD4625	Phase 3
0.756	Intermediate Similarity	NPD1653	Approved
0.7543	Intermediate Similarity	NPD5711	Approved
0.7543	Intermediate Similarity	NPD5710	Approved
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7516	Intermediate Similarity	NPD4908	Phase 1
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD1243	Approved
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8151	Discontinued
0.747	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7461	Intermediate Similarity	NPD7584	Approved
0.7455	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6651	Approved
0.7447	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5953	Discontinued
0.743	Intermediate Similarity	NPD7286	Phase 2
0.7425	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2313	Discontinued
0.741	Intermediate Similarity	NPD6190	Approved
0.7398	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7783	Phase 2
0.7396	Intermediate Similarity	NPD7696	Phase 3
0.7396	Intermediate Similarity	NPD7698	Approved
0.7396	Intermediate Similarity	NPD7697	Approved
0.7391	Intermediate Similarity	NPD5124	Phase 1
0.7391	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8434	Phase 2
0.7391	Intermediate Similarity	NPD1933	Approved
0.7381	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2344	Approved
0.7362	Intermediate Similarity	NPD7033	Discontinued
0.7358	Intermediate Similarity	NPD7870	Phase 2
0.7358	Intermediate Similarity	NPD7871	Phase 2
0.7349	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7229	Phase 3
0.7344	Intermediate Similarity	NPD6823	Phase 2
0.7342	Intermediate Similarity	NPD9494	Approved
0.734	Intermediate Similarity	NPD6534	Approved
0.734	Intermediate Similarity	NPD6535	Approved
0.7333	Intermediate Similarity	NPD7701	Phase 2
0.7329	Intermediate Similarity	NPD4060	Phase 1
0.7308	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7240	Approved
0.7292	Intermediate Similarity	NPD2493	Approved
0.7292	Intermediate Similarity	NPD2494	Approved
0.729	Intermediate Similarity	NPD1610	Phase 2
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6674	Discontinued
0.7289	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7874	Approved
0.7259	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8455	Phase 2
0.7229	Intermediate Similarity	NPD2424	Discontinued
0.7225	Intermediate Similarity	NPD7700	Phase 2
0.7225	Intermediate Similarity	NPD7699	Phase 2
0.7225	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7801	Approved
0.7212	Intermediate Similarity	NPD5408	Approved
0.7212	Intermediate Similarity	NPD5404	Approved
0.7212	Intermediate Similarity	NPD5405	Approved
0.7212	Intermediate Similarity	NPD5406	Approved
0.7211	Intermediate Similarity	NPD4361	Phase 2
0.7211	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7207	Intermediate Similarity	NPD5242	Approved
0.7205	Intermediate Similarity	NPD3268	Approved
0.7202	Intermediate Similarity	NPD2309	Approved
0.7202	Intermediate Similarity	NPD3450	Approved
0.7202	Intermediate Similarity	NPD3452	Approved
0.72	Intermediate Similarity	NPD4288	Approved
0.7191	Intermediate Similarity	NPD8127	Discontinued
0.7184	Intermediate Similarity	NPD6844	Discontinued
0.7179	Intermediate Similarity	NPD4583	Approved
0.7179	Intermediate Similarity	NPD1201	Approved
0.7179	Intermediate Similarity	NPD4582	Approved
0.7174	Intermediate Similarity	NPD7549	Discontinued
0.717	Intermediate Similarity	NPD2798	Approved
0.7157	Intermediate Similarity	NPD7907	Approved
0.7143	Intermediate Similarity	NPD4111	Phase 1
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD4665	Approved
0.7135	Intermediate Similarity	NPD6273	Approved
0.7128	Intermediate Similarity	NPD4287	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