NPASS Compound

Structure

NPC102904 OpenBabel07101718302D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 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 -1.7321 1.0000 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 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 1.0000 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 -0.5000 0.0000 C 0 0 1 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 -2.5981 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 1 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 11 1 1 0 0 0 14 22 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.12
Volume:	305.051
LogP:	2.953
LogD:	3.227
LogS:	-3.794
# Rotatable Bonds:	3
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.911
Synthetic Accessibility Score:	2.753
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.713
MDCK Permeability:	1.8516770069254562e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	96.1915512084961%
Volume Distribution (VD):	0.8
Pgp-substrate:	4.884100914001465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.804
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.792
CYP2C19-substrate:	0.553
CYP2C9-inhibitor:	0.732
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.437
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.673
CYP3A4-substrate:	0.676

ADMET: Excretion

Clearance (CL):	14.154
Half-life (T1/2):	0.756

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.707
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.821
Skin Sensitization:	0.925
Carcinogencity:	0.465
Eye Corrosion:	0.011
Eye Irritation:	0.885
Respiratory Toxicity:	0.816

Download Data

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

Natural Product: NPC102904

Natural Product ID:	NPC102904
*Common Name:**	(2S)-6,4'-Dihydroxy-7,3'-Dimethoxyflavan
IUPAC Name:	(2S)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3,4-dihydro-2H-chromen-6-ol
Synonyms:
Standard InCHIKey:	JKEOWRFBUPMWAZ-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C17H18O5/c1-20-16-8-11(3-5-12(16)18)14-6-4-10-7-13(19)17(21-2)9-15(10)22-14/h3,5,7-9,14,18-19H,4,6H2,1-2H3/t14-/m0/s1
SMILES:	COc1cc(ccc1O)[C@@H]1CCc2c(O1)cc(c(c2)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409055
PubChem CID:	71746244
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	n.a.	stem	n.a.	PMID[21919533]
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23795891]
NPO12425	Combretum griffithii	Species	Combretaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	76480.0	nM	PMID[503174]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	90070.0	nM	PMID[503174]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	69000.0	nM	PMID[503174]

☑ 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 NPC102904 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	437
0.1-0.2	1701
0.2-0.3	5264
0.3-0.4	12817
0.4-0.5	4664
0.5-0.6	4108
0.6-0.7	5952
0.7-0.8	5679
0.8-0.85	1150
0.85-0.9	588
0.9-0.95	260
0.95-1	77

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474282
1.0	High Similarity	NPC326797
1.0	High Similarity	NPC103976
1.0	High Similarity	NPC107551
1.0	High Similarity	NPC176051
0.9847	High Similarity	NPC276490
0.9846	High Similarity	NPC112246
0.9846	High Similarity	NPC470356
0.9846	High Similarity	NPC121812
0.9846	High Similarity	NPC94750
0.9846	High Similarity	NPC112939
0.9846	High Similarity	NPC474206
0.9774	High Similarity	NPC471389
0.9773	High Similarity	NPC127218
0.9773	High Similarity	NPC245207
0.9773	High Similarity	NPC319647
0.9773	High Similarity	NPC25966
0.9771	High Similarity	NPC227503
0.9771	High Similarity	NPC16435
0.9771	High Similarity	NPC472336
0.9771	High Similarity	NPC230734
0.9771	High Similarity	NPC472334
0.9771	High Similarity	NPC474639
0.9771	High Similarity	NPC306441
0.9701	High Similarity	NPC107161
0.9697	High Similarity	NPC211549
0.9695	High Similarity	NPC47398
0.9695	High Similarity	NPC61946
0.9695	High Similarity	NPC195022
0.9695	High Similarity	NPC151224
0.9695	High Similarity	NPC260898
0.9695	High Similarity	NPC234333
0.9695	High Similarity	NPC472337
0.9692	High Similarity	NPC11060
0.9627	High Similarity	NPC247291
0.9624	High Similarity	NPC471388
0.9621	High Similarity	NPC162659
0.9621	High Similarity	NPC248727
0.9621	High Similarity	NPC173660
0.9621	High Similarity	NPC265433
0.9621	High Similarity	NPC302701
0.9621	High Similarity	NPC270456
0.9621	High Similarity	NPC269091
0.9618	High Similarity	NPC106215
0.9618	High Similarity	NPC317380
0.9615	High Similarity	NPC86655
0.9615	High Similarity	NPC202762
0.9615	High Similarity	NPC127624
0.9559	High Similarity	NPC12641
0.9559	High Similarity	NPC50250
0.9559	High Similarity	NPC280092
0.9559	High Similarity	NPC45257
0.9559	High Similarity	NPC93323
0.9552	High Similarity	NPC309124
0.9552	High Similarity	NPC27495
0.9552	High Similarity	NPC184797
0.9552	High Similarity	NPC160283
0.9552	High Similarity	NPC254759
0.9552	High Similarity	NPC259519
0.9545	High Similarity	NPC164787
0.9545	High Similarity	NPC134968
0.9545	High Similarity	NPC473413
0.9542	High Similarity	NPC229442
0.9542	High Similarity	NPC168059
0.9542	High Similarity	NPC475840
0.9542	High Similarity	NPC263064
0.9485	High Similarity	NPC102044
0.9485	High Similarity	NPC47633
0.9485	High Similarity	NPC85264
0.9478	High Similarity	NPC292882
0.9478	High Similarity	NPC70682
0.9478	High Similarity	NPC473739
0.9478	High Similarity	NPC232164
0.9478	High Similarity	NPC260741
0.9478	High Similarity	NPC236306
0.9474	High Similarity	NPC470802
0.9474	High Similarity	NPC234952
0.947	High Similarity	NPC310854
0.947	High Similarity	NPC170694
0.9466	High Similarity	NPC185604
0.9466	High Similarity	NPC126029
0.9466	High Similarity	NPC61477
0.9466	High Similarity	NPC261619
0.9466	High Similarity	NPC201587
0.9466	High Similarity	NPC253105
0.9466	High Similarity	NPC219876
0.9466	High Similarity	NPC15658
0.9466	High Similarity	NPC78770
0.9462	High Similarity	NPC214860
0.9462	High Similarity	NPC311680
0.9462	High Similarity	NPC234488
0.9462	High Similarity	NPC299221
0.9462	High Similarity	NPC51840
0.9416	High Similarity	NPC63879
0.9407	High Similarity	NPC22317
0.9389	High Similarity	NPC42760
0.9389	High Similarity	NPC220825
0.9389	High Similarity	NPC472597
0.9389	High Similarity	NPC268342
0.9389	High Similarity	NPC268266
0.9385	High Similarity	NPC58164
0.9385	High Similarity	NPC10225
0.9385	High Similarity	NPC45824
0.9353	High Similarity	NPC16269
0.9353	High Similarity	NPC227902
0.9353	High Similarity	NPC21776
0.9343	High Similarity	NPC477616
0.9343	High Similarity	NPC81638
0.9338	High Similarity	NPC35216
0.9338	High Similarity	NPC311530
0.9333	High Similarity	NPC32630
0.9323	High Similarity	NPC478085
0.9318	High Similarity	NPC470752
0.9318	High Similarity	NPC35932
0.9318	High Similarity	NPC6451
0.9318	High Similarity	NPC160991
0.9318	High Similarity	NPC7903
0.9318	High Similarity	NPC16208
0.9318	High Similarity	NPC184447
0.9313	High Similarity	NPC472338
0.9313	High Similarity	NPC91291
0.9313	High Similarity	NPC220935
0.9308	High Similarity	NPC31707
0.9308	High Similarity	NPC226331
0.9308	High Similarity	NPC266691
0.9308	High Similarity	NPC46274
0.9286	High Similarity	NPC281549
0.9286	High Similarity	NPC175976
0.9275	High Similarity	NPC473108
0.927	High Similarity	NPC59841
0.927	High Similarity	NPC2613
0.927	High Similarity	NPC204347
0.927	High Similarity	NPC475891
0.9254	High Similarity	NPC201357
0.9254	High Similarity	NPC255147
0.9254	High Similarity	NPC281521
0.9242	High Similarity	NPC12275
0.9242	High Similarity	NPC45715
0.9242	High Similarity	NPC474356
0.9242	High Similarity	NPC309787
0.9242	High Similarity	NPC232275
0.9237	High Similarity	NPC170844
0.9237	High Similarity	NPC476968
0.9237	High Similarity	NPC222004
0.9237	High Similarity	NPC210623
0.9237	High Similarity	NPC86030
0.9237	High Similarity	NPC273295
0.9237	High Similarity	NPC212015
0.9237	High Similarity	NPC285339
0.9237	High Similarity	NPC202582
0.9237	High Similarity	NPC226788
0.9237	High Similarity	NPC190629
0.9237	High Similarity	NPC3439
0.9237	High Similarity	NPC218856
0.9237	High Similarity	NPC5851
0.9237	High Similarity	NPC470258
0.9231	High Similarity	NPC124452
0.9231	High Similarity	NPC210355
0.9231	High Similarity	NPC282000
0.9231	High Similarity	NPC159968
0.9231	High Similarity	NPC216836
0.9231	High Similarity	NPC236791
0.9231	High Similarity	NPC293054
0.9231	High Similarity	NPC324112
0.9231	High Similarity	NPC250432
0.9231	High Similarity	NPC169474
0.9231	High Similarity	NPC74817
0.9231	High Similarity	NPC246620
0.9231	High Similarity	NPC5447
0.9231	High Similarity	NPC82679
0.9214	High Similarity	NPC101376
0.9209	High Similarity	NPC307466
0.9209	High Similarity	NPC475096
0.9203	High Similarity	NPC252169
0.9197	High Similarity	NPC265075
0.9197	High Similarity	NPC87725
0.9197	High Similarity	NPC178054
0.9197	High Similarity	NPC263261
0.9191	High Similarity	NPC22517
0.9185	High Similarity	NPC476698
0.9179	High Similarity	NPC474478
0.9167	High Similarity	NPC224157
0.9167	High Similarity	NPC192687
0.916	High Similarity	NPC222572
0.916	High Similarity	NPC206615
0.916	High Similarity	NPC245826
0.916	High Similarity	NPC98631
0.916	High Similarity	NPC470213
0.916	High Similarity	NPC72529
0.916	High Similarity	NPC252307
0.916	High Similarity	NPC474178
0.916	High Similarity	NPC186843
0.916	High Similarity	NPC87224
0.9154	High Similarity	NPC223136
0.9154	High Similarity	NPC28730
0.9154	High Similarity	NPC103823
0.9154	High Similarity	NPC214406
0.9154	High Similarity	NPC44748
0.9154	High Similarity	NPC18924
0.9154	High Similarity	NPC78974

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 NPC102904 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	890
0.2-0.3	1973
0.3-0.4	2711
0.4-0.5	1529
0.5-0.6	842
0.6-0.7	644
0.7-0.8	153
0.8-0.85	13
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9466	High Similarity	NPD1612	Clinical (unspecified phase)
0.9466	High Similarity	NPD1613	Approved
0.9308	High Similarity	NPD1529	Clinical (unspecified phase)
0.9237	High Similarity	NPD3027	Phase 3
0.9231	High Similarity	NPD1530	Clinical (unspecified phase)
0.8593	High Similarity	NPD4908	Phase 1
0.8581	High Similarity	NPD1934	Approved
0.8519	High Similarity	NPD2861	Phase 2
0.8485	Intermediate Similarity	NPD1610	Phase 2
0.8467	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1653	Approved
0.84	Intermediate Similarity	NPD2801	Approved
0.84	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1548	Phase 1
0.817	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6166	Phase 2
0.8153	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4625	Phase 3
0.8116	Intermediate Similarity	NPD3018	Phase 2
0.8088	Intermediate Similarity	NPD4749	Approved
0.7956	Intermediate Similarity	NPD2983	Phase 2
0.7956	Intermediate Similarity	NPD2982	Phase 2
0.7955	Intermediate Similarity	NPD6671	Approved
0.795	Intermediate Similarity	NPD7074	Phase 3
0.7943	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD3882	Suspended
0.7923	Intermediate Similarity	NPD228	Approved
0.7919	Intermediate Similarity	NPD1511	Approved
0.7891	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7054	Approved
0.7888	Intermediate Similarity	NPD5844	Phase 1
0.7883	Intermediate Similarity	NPD2981	Phase 2
0.784	Intermediate Similarity	NPD7472	Approved
0.7834	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7815	Intermediate Similarity	NPD1512	Approved
0.781	Intermediate Similarity	NPD1091	Approved
0.7805	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD5283	Phase 1
0.7785	Intermediate Similarity	NPD5494	Approved
0.777	Intermediate Similarity	NPD6674	Discontinued
0.7756	Intermediate Similarity	NPD3817	Phase 2
0.7708	Intermediate Similarity	NPD4060	Phase 1
0.7708	Intermediate Similarity	NPD1558	Phase 1
0.7698	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6797	Phase 2
0.7682	Intermediate Similarity	NPD7213	Phase 3
0.7682	Intermediate Similarity	NPD7212	Phase 2
0.7671	Intermediate Similarity	NPD4538	Approved
0.7671	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4536	Approved
0.7651	Intermediate Similarity	NPD1652	Phase 2
0.7636	Intermediate Similarity	NPD7251	Discontinued
0.7635	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD7266	Discontinued
0.7632	Intermediate Similarity	NPD7447	Phase 1
0.7628	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD7199	Phase 2
0.7613	Intermediate Similarity	NPD4678	Approved
0.7613	Intermediate Similarity	NPD4675	Approved
0.7613	Intermediate Similarity	NPD4380	Phase 2
0.7607	Intermediate Similarity	NPD7228	Approved
0.7595	Intermediate Similarity	NPD4965	Approved
0.7595	Intermediate Similarity	NPD4966	Approved
0.7595	Intermediate Similarity	NPD4967	Phase 2
0.759	Intermediate Similarity	NPD7808	Phase 3
0.759	Intermediate Similarity	NPD7549	Discontinued
0.7586	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3620	Phase 2
0.7584	Intermediate Similarity	NPD1549	Phase 2
0.7582	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1465	Phase 2
0.7576	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD2684	Approved
0.7554	Intermediate Similarity	NPD422	Phase 1
0.755	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7075	Discontinued
0.7547	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD968	Approved
0.7534	Intermediate Similarity	NPD5124	Phase 1
0.7534	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD5177	Phase 3
0.7531	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD8651	Approved
0.7517	Intermediate Similarity	NPD3540	Phase 1
0.7517	Intermediate Similarity	NPD6233	Phase 2
0.7516	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD3022	Approved
0.75	Intermediate Similarity	NPD5960	Phase 3
0.7481	Intermediate Similarity	NPD290	Approved
0.7468	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7843	Approved
0.745	Intermediate Similarity	NPD6099	Approved
0.745	Intermediate Similarity	NPD6100	Approved
0.745	Intermediate Similarity	NPD3539	Phase 1
0.7448	Intermediate Similarity	NPD6798	Discontinued
0.7438	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3705	Approved
0.7426	Intermediate Similarity	NPD7157	Approved
0.7421	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5402	Approved
0.7413	Intermediate Similarity	NPD6584	Phase 3
0.7413	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8053	Approved
0.7396	Intermediate Similarity	NPD8054	Approved
0.7386	Intermediate Similarity	NPD5058	Phase 3
0.7383	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6232	Discontinued
0.7357	Intermediate Similarity	NPD3496	Discontinued
0.7342	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2796	Approved
0.7325	Intermediate Similarity	NPD4005	Discontinued
0.7324	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6559	Discontinued
0.732	Intermediate Similarity	NPD6190	Approved
0.732	Intermediate Similarity	NPD2677	Approved
0.7312	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3060	Approved
0.7297	Intermediate Similarity	NPD6355	Discontinued
0.729	Intermediate Similarity	NPD4123	Phase 3
0.7286	Intermediate Similarity	NPD5846	Approved
0.7286	Intermediate Similarity	NPD6516	Phase 2
0.7273	Intermediate Similarity	NPD6696	Suspended
0.7267	Intermediate Similarity	NPD7906	Approved
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.726	Intermediate Similarity	NPD7095	Approved
0.7256	Intermediate Similarity	NPD3787	Discontinued
0.7255	Intermediate Similarity	NPD3892	Phase 2
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3750	Approved
0.7255	Intermediate Similarity	NPD6331	Phase 2
0.725	Intermediate Similarity	NPD7819	Suspended
0.7246	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2424	Discontinued
0.7231	Intermediate Similarity	NPD846	Approved
0.7231	Intermediate Similarity	NPD940	Approved
0.7229	Intermediate Similarity	NPD7473	Discontinued
0.7226	Intermediate Similarity	NPD4357	Discontinued
0.7226	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1774	Approved
0.7226	Intermediate Similarity	NPD6799	Approved
0.7219	Intermediate Similarity	NPD2935	Discontinued
0.7214	Intermediate Similarity	NPD1357	Approved
0.7209	Intermediate Similarity	NPD4663	Approved
0.7203	Intermediate Similarity	NPD6582	Phase 2
0.7203	Intermediate Similarity	NPD6583	Phase 3
0.7195	Intermediate Similarity	NPD6959	Discontinued
0.7194	Intermediate Similarity	NPD5536	Phase 2
0.7192	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4162	Approved
0.719	Intermediate Similarity	NPD4237	Approved
0.719	Intermediate Similarity	NPD4236	Phase 3
0.7188	Intermediate Similarity	NPD6801	Discontinued
0.7181	Intermediate Similarity	NPD230	Phase 1
0.7181	Intermediate Similarity	NPD5735	Approved
0.7179	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5762	Approved
0.7171	Intermediate Similarity	NPD5763	Approved
0.7171	Intermediate Similarity	NPD1375	Discontinued
0.7169	Intermediate Similarity	NPD27	Approved
0.7169	Intermediate Similarity	NPD2489	Approved
0.7161	Intermediate Similarity	NPD7124	Phase 2
0.7154	Intermediate Similarity	NPD1242	Phase 1
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5929	Approved
0.7143	Intermediate Similarity	NPD7466	Approved
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD4535	Phase 3
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7313	Approved
0.7135	Intermediate Similarity	NPD7311	Approved
0.7135	Intermediate Similarity	NPD7312	Approved
0.7135	Intermediate Similarity	NPD7310	Approved
0.7135	Intermediate Similarity	NPD4577	Approved
0.7135	Intermediate Similarity	NPD4578	Approved
0.7134	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7411	Suspended
0.7118	Intermediate Similarity	NPD7240	Approved
0.7114	Intermediate Similarity	NPD1240	Approved
0.7114	Intermediate Similarity	NPD2238	Phase 2
0.7114	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4750	Phase 3
0.7108	Intermediate Similarity	NPD2970	Approved
0.7108	Intermediate Similarity	NPD2969	Approved
0.7105	Intermediate Similarity	NPD6032	Approved
0.7099	Intermediate Similarity	NPD2563	Approved
0.7099	Intermediate Similarity	NPD2560	Approved
0.7099	Intermediate Similarity	NPD291	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