NPASS Compound

Structure

NPC306441 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -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 2.5981 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 0.0000 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 2.5981 0.5000 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 -3.4641 -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 2 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 0.5000 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 0.5000 0.0000 C 0 0 2 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 -1.7321 2.0000 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 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 17 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 16 2 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 11 21 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 6 0 0 0 15 22 1 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 18 10 1 6 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.13
Volume:	331.137
LogP:	2.705
LogD:	2.882
LogS:	-4.02
# Rotatable Bonds:	4
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.895
Synthetic Accessibility Score:	3.089
Fsp3:	0.333
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:	-5.012
MDCK Permeability:	1.578394221724011e-05
Pgp-inhibitor:	0.227
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.802
Plasma Protein Binding (PPB):	90.7655258178711%
Volume Distribution (VD):	0.765
Pgp-substrate:	9.80621337890625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.152
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.147
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.373
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.177
CYP2D6-substrate:	0.905
CYP3A4-inhibitor:	0.725
CYP3A4-substrate:	0.778

ADMET: Excretion

Clearance (CL):	9.775
Half-life (T1/2):	0.605

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.704
AMES Toxicity:	0.116
Rat Oral Acute Toxicity:	0.105
Maximum Recommended Daily Dose:	0.245
Skin Sensitization:	0.396
Carcinogencity:	0.149
Eye Corrosion:	0.003
Eye Irritation:	0.124
Respiratory Toxicity:	0.66

Download Data

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

Natural Product: NPC306441

Natural Product ID:	NPC306441
*Common Name:**	(-)-4'-Hydroxy-5,7,3'-Trimethoxyflavan-3-Ol
IUPAC Name:	(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-chromen-3-ol
Synonyms:
Standard InCHIKey:	IJCWCJRLHJAVFD-RDTXWAMCSA-N
Standard InCHI:	InChI=1S/C18H20O6/c1-21-11-7-15(22-2)12-9-14(20)18(24-16(12)8-11)10-4-5-13(19)17(6-10)23-3/h4-8,14,18-20H,9H2,1-3H3/t14-,18-/m1/s1
SMILES:	COc1cc(c2C[C@H]([C@@H](c3ccc(c(c3)OC)O)Oc2c1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465960
PubChem CID:	6482487
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins

*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
NPO23473	Cinnamomum kotoense	Species	Lauraceae	Eukaryota	stem wood	n.a.	n.a.	PMID[16180806]
NPO23473	Cinnamomum kotoense	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[16792412]
NPO23473	Cinnamomum kotoense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18489163]
NPO23473	Cinnamomum kotoense	Species	Lauraceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	150600.0	nM	PMID[521856]

☑ 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 NPC306441 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	421
0.1-0.2	1604
0.2-0.3	4866
0.3-0.4	12408
0.4-0.5	5413
0.5-0.6	4018
0.6-0.7	5769
0.7-0.8	6014
0.8-0.85	1146
0.85-0.9	625
0.9-0.95	327
0.95-1	86

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC16435
0.9922	High Similarity	NPC470356
0.9922	High Similarity	NPC112939
0.9922	High Similarity	NPC94750
0.9922	High Similarity	NPC121812
0.9922	High Similarity	NPC260898
0.9922	High Similarity	NPC47398
0.9922	High Similarity	NPC112246
0.9922	High Similarity	NPC474206
0.9922	High Similarity	NPC234333
0.9922	High Similarity	NPC61946
0.9846	High Similarity	NPC227503
0.9846	High Similarity	NPC302701
0.9846	High Similarity	NPC230734
0.9846	High Similarity	NPC269091
0.9846	High Similarity	NPC474639
0.9771	High Similarity	NPC326797
0.9771	High Similarity	NPC474282
0.9771	High Similarity	NPC107551
0.9771	High Similarity	NPC103976
0.9771	High Similarity	NPC176051
0.9771	High Similarity	NPC211549
0.9771	High Similarity	NPC102904
0.9769	High Similarity	NPC164787
0.9769	High Similarity	NPC151224
0.9767	High Similarity	NPC263064
0.9767	High Similarity	NPC11060
0.9767	High Similarity	NPC475840
0.9699	High Similarity	NPC471389
0.9695	High Similarity	NPC248727
0.9695	High Similarity	NPC265433
0.9695	High Similarity	NPC472336
0.9695	High Similarity	NPC270456
0.9695	High Similarity	NPC162659
0.9695	High Similarity	NPC472334
0.9695	High Similarity	NPC470802
0.9692	High Similarity	NPC317380
0.9692	High Similarity	NPC170694
0.969	High Similarity	NPC127624
0.969	High Similarity	NPC86655
0.969	High Similarity	NPC261619
0.969	High Similarity	NPC78770
0.969	High Similarity	NPC126029
0.969	High Similarity	NPC253105
0.969	High Similarity	NPC61477
0.969	High Similarity	NPC15658
0.969	High Similarity	NPC202762
0.969	High Similarity	NPC185604
0.969	High Similarity	NPC219876
0.969	High Similarity	NPC201587
0.9624	High Similarity	NPC309124
0.9624	High Similarity	NPC184797
0.9621	High Similarity	NPC276490
0.9618	High Similarity	NPC472337
0.9618	High Similarity	NPC473413
0.9615	High Similarity	NPC168059
0.9615	High Similarity	NPC229442
0.9612	High Similarity	NPC268266
0.9612	High Similarity	NPC42760
0.9612	High Similarity	NPC268342
0.9612	High Similarity	NPC472597
0.9612	High Similarity	NPC220825
0.9549	High Similarity	NPC232164
0.9549	High Similarity	NPC319647
0.9549	High Similarity	NPC127218
0.9549	High Similarity	NPC471388
0.9549	High Similarity	NPC260741
0.9549	High Similarity	NPC245207
0.9549	High Similarity	NPC236306
0.9549	High Similarity	NPC25966
0.9549	High Similarity	NPC70682
0.9549	High Similarity	NPC473739
0.9545	High Similarity	NPC234952
0.9542	High Similarity	NPC478085
0.9538	High Similarity	NPC160991
0.9538	High Similarity	NPC16208
0.9538	High Similarity	NPC7903
0.9538	High Similarity	NPC184447
0.9538	High Similarity	NPC470752
0.9538	High Similarity	NPC35932
0.9535	High Similarity	NPC472338
0.9481	High Similarity	NPC107161
0.9478	High Similarity	NPC22317
0.947	High Similarity	NPC195022
0.9462	High Similarity	NPC309787
0.9457	High Similarity	NPC3439
0.9457	High Similarity	NPC212015
0.9457	High Similarity	NPC470258
0.9457	High Similarity	NPC285339
0.9457	High Similarity	NPC218856
0.9457	High Similarity	NPC202582
0.9457	High Similarity	NPC476968
0.9457	High Similarity	NPC190629
0.9457	High Similarity	NPC222004
0.9457	High Similarity	NPC273295
0.9457	High Similarity	NPC226788
0.9457	High Similarity	NPC5851
0.9457	High Similarity	NPC170844
0.9457	High Similarity	NPC86030
0.9457	High Similarity	NPC210623
0.9416	High Similarity	NPC475096
0.9412	High Similarity	NPC81638
0.9407	High Similarity	NPC178054
0.9407	High Similarity	NPC35216
0.9407	High Similarity	NPC247291
0.9407	High Similarity	NPC87725
0.9407	High Similarity	NPC263261
0.9403	High Similarity	NPC22517
0.9403	High Similarity	NPC32630
0.9398	High Similarity	NPC173660
0.9394	High Similarity	NPC310854
0.9394	High Similarity	NPC106215
0.9385	High Similarity	NPC91291
0.938	High Similarity	NPC206615
0.938	High Similarity	NPC245826
0.938	High Similarity	NPC31707
0.938	High Similarity	NPC252307
0.938	High Similarity	NPC46274
0.938	High Similarity	NPC470213
0.938	High Similarity	NPC72529
0.938	High Similarity	NPC226331
0.938	High Similarity	NPC98631
0.938	High Similarity	NPC474178
0.938	High Similarity	NPC186843
0.9348	High Similarity	NPC190714
0.9348	High Similarity	NPC99515
0.9348	High Similarity	NPC125755
0.9343	High Similarity	NPC12641
0.9343	High Similarity	NPC171932
0.9343	High Similarity	NPC280092
0.9343	High Similarity	NPC473108
0.9343	High Similarity	NPC50250
0.9343	High Similarity	NPC45257
0.9343	High Similarity	NPC93323
0.9343	High Similarity	NPC28440
0.9338	High Similarity	NPC189115
0.9338	High Similarity	NPC475891
0.9338	High Similarity	NPC204347
0.9338	High Similarity	NPC475084
0.9338	High Similarity	NPC2613
0.9338	High Similarity	NPC59841
0.9333	High Similarity	NPC266197
0.9333	High Similarity	NPC259519
0.9333	High Similarity	NPC254759
0.9333	High Similarity	NPC160283
0.9333	High Similarity	NPC291101
0.9333	High Similarity	NPC27495
0.9328	High Similarity	NPC474390
0.9323	High Similarity	NPC256262
0.9323	High Similarity	NPC134968
0.9313	High Similarity	NPC469613
0.9313	High Similarity	NPC470096
0.9313	High Similarity	NPC474017
0.9313	High Similarity	NPC470095
0.9313	High Similarity	NPC469625
0.9313	High Similarity	NPC103799
0.9313	High Similarity	NPC30043
0.9308	High Similarity	NPC469951
0.9308	High Similarity	NPC469963
0.9302	High Similarity	NPC147821
0.9302	High Similarity	NPC324112
0.9302	High Similarity	NPC282000
0.9302	High Similarity	NPC169474
0.9302	High Similarity	NPC118787
0.9302	High Similarity	NPC210355
0.9302	High Similarity	NPC74817
0.9302	High Similarity	NPC159968
0.9302	High Similarity	NPC183181
0.9302	High Similarity	NPC111247
0.9302	High Similarity	NPC293054
0.9302	High Similarity	NPC163332
0.9302	High Similarity	NPC246620
0.9302	High Similarity	NPC5447
0.9302	High Similarity	NPC41706
0.9302	High Similarity	NPC250432
0.9302	High Similarity	NPC319625
0.9302	High Similarity	NPC82679
0.9302	High Similarity	NPC474119
0.9302	High Similarity	NPC124452
0.9302	High Similarity	NPC236791
0.9302	High Similarity	NPC242032
0.9302	High Similarity	NPC292056
0.9281	High Similarity	NPC474397
0.9281	High Similarity	NPC227902
0.9275	High Similarity	NPC161700
0.9275	High Similarity	NPC277867
0.927	High Similarity	NPC47633
0.927	High Similarity	NPC85264
0.927	High Similarity	NPC102044
0.927	High Similarity	NPC477616
0.9265	High Similarity	NPC83375
0.9265	High Similarity	NPC265075
0.9265	High Similarity	NPC224876
0.9265	High Similarity	NPC469661
0.9265	High Similarity	NPC311530
0.9259	High Similarity	NPC292882
0.9248	High Similarity	NPC287745
0.9237	High Similarity	NPC234488
0.9237	High Similarity	NPC299221
0.9237	High Similarity	NPC214860

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 NPC306441 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	878
0.2-0.3	1953
0.3-0.4	2693
0.4-0.5	1530
0.5-0.6	870
0.6-0.7	659
0.7-0.8	175
0.8-0.85	11
0.85-0.9	4
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.969	High Similarity	NPD1612	Clinical (unspecified phase)
0.969	High Similarity	NPD1613	Approved
0.9457	High Similarity	NPD3027	Phase 3
0.938	High Similarity	NPD1529	Clinical (unspecified phase)
0.9302	High Similarity	NPD1530	Clinical (unspecified phase)
0.8657	High Similarity	NPD4908	Phase 1
0.8639	High Similarity	NPD1934	Approved
0.855	High Similarity	NPD1610	Phase 2
0.8529	High Similarity	NPD4907	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD1548	Phase 1
0.8367	Intermediate Similarity	NPD1653	Approved
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8309	Intermediate Similarity	NPD2861	Phase 2
0.8224	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2801	Approved
0.8188	Intermediate Similarity	NPD4625	Phase 3
0.8175	Intermediate Similarity	NPD3018	Phase 2
0.8148	Intermediate Similarity	NPD4749	Approved
0.8129	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7074	Phase 3
0.8069	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7054	Approved
0.8015	Intermediate Similarity	NPD2983	Phase 2
0.8015	Intermediate Similarity	NPD2982	Phase 2
0.8	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD1091	Approved
0.7987	Intermediate Similarity	NPD3818	Discontinued
0.7987	Intermediate Similarity	NPD3882	Suspended
0.7984	Intermediate Similarity	NPD228	Approved
0.7973	Intermediate Similarity	NPD1511	Approved
0.7945	Intermediate Similarity	NPD6674	Discontinued
0.7941	Intermediate Similarity	NPD2981	Phase 2
0.7885	Intermediate Similarity	NPD6234	Discontinued
0.7867	Intermediate Similarity	NPD1512	Approved
0.7863	Intermediate Similarity	NPD5283	Phase 1
0.7847	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD4538	Approved
0.7847	Intermediate Similarity	NPD4536	Approved
0.784	Intermediate Similarity	NPD6797	Phase 2
0.7826	Intermediate Similarity	NPD5844	Phase 1
0.7823	Intermediate Similarity	NPD1652	Phase 2
0.7808	Intermediate Similarity	NPD7266	Discontinued
0.7806	Intermediate Similarity	NPD3817	Phase 2
0.7792	Intermediate Similarity	NPD37	Approved
0.7791	Intermediate Similarity	NPD7251	Discontinued
0.7785	Intermediate Similarity	NPD7199	Phase 2
0.7778	Intermediate Similarity	NPD4380	Phase 2
0.7764	Intermediate Similarity	NPD7228	Approved
0.7762	Intermediate Similarity	NPD3620	Phase 2
0.7762	Intermediate Similarity	NPD1558	Phase 1
0.7762	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD4060	Phase 1
0.7756	Intermediate Similarity	NPD4966	Approved
0.7756	Intermediate Similarity	NPD4965	Approved
0.7756	Intermediate Similarity	NPD4967	Phase 2
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD2684	Approved
0.7746	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6671	Approved
0.7744	Intermediate Similarity	NPD7808	Phase 3
0.7744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7213	Phase 3
0.7733	Intermediate Similarity	NPD7212	Phase 2
0.773	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5124	Phase 1
0.7707	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD5177	Phase 3
0.7698	Intermediate Similarity	NPD8651	Approved
0.7687	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7447	Phase 1
0.7674	Intermediate Similarity	NPD290	Approved
0.7671	Intermediate Similarity	NPD5588	Approved
0.7671	Intermediate Similarity	NPD5960	Phase 3
0.7662	Intermediate Similarity	NPD4678	Approved
0.7662	Intermediate Similarity	NPD4675	Approved
0.7652	Intermediate Similarity	NPD7843	Approved
0.7635	Intermediate Similarity	NPD1549	Phase 2
0.7628	Intermediate Similarity	NPD1465	Phase 2
0.7612	Intermediate Similarity	NPD7157	Approved
0.761	Intermediate Similarity	NPD5494	Approved
0.7609	Intermediate Similarity	NPD422	Phase 1
0.76	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7075	Discontinued
0.7595	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3540	Phase 1
0.7566	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3022	Approved
0.7557	Intermediate Similarity	NPD3021	Approved
0.755	Intermediate Similarity	NPD5058	Phase 3
0.7516	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3539	Phase 1
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD6099	Approved
0.7484	Intermediate Similarity	NPD4005	Discontinued
0.7484	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2677	Approved
0.7482	Intermediate Similarity	NPD3705	Approved
0.747	Intermediate Similarity	NPD6559	Discontinued
0.7467	Intermediate Similarity	NPD3060	Approved
0.7465	Intermediate Similarity	NPD6584	Phase 3
0.7464	Intermediate Similarity	NPD5846	Approved
0.7464	Intermediate Similarity	NPD6516	Phase 2
0.744	Intermediate Similarity	NPD8054	Approved
0.744	Intermediate Similarity	NPD8053	Approved
0.7432	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7549	Discontinued
0.7417	Intermediate Similarity	NPD3892	Phase 2
0.7407	Intermediate Similarity	NPD6232	Discontinued
0.7403	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2424	Discontinued
0.7394	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1357	Approved
0.7389	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1774	Approved
0.7383	Intermediate Similarity	NPD2796	Approved
0.7376	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6190	Approved
0.7358	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5402	Approved
0.7351	Intermediate Similarity	NPD4236	Phase 3
0.7351	Intermediate Similarity	NPD4162	Approved
0.7351	Intermediate Similarity	NPD4237	Approved
0.7347	Intermediate Similarity	NPD6355	Discontinued
0.7347	Intermediate Similarity	NPD5735	Approved
0.7342	Intermediate Similarity	NPD6801	Discontinued
0.7338	Intermediate Similarity	NPD4123	Phase 3
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5763	Approved
0.7333	Intermediate Similarity	NPD5762	Approved
0.7329	Intermediate Similarity	NPD6233	Phase 2
0.7328	Intermediate Similarity	NPD968	Approved
0.7317	Intermediate Similarity	NPD27	Approved
0.7317	Intermediate Similarity	NPD2489	Approved
0.7315	Intermediate Similarity	NPD7033	Discontinued
0.7315	Intermediate Similarity	NPD1510	Phase 2
0.731	Intermediate Similarity	NPD7095	Approved
0.7303	Intermediate Similarity	NPD4628	Phase 3
0.7303	Intermediate Similarity	NPD6331	Phase 2
0.7303	Intermediate Similarity	NPD3750	Approved
0.7303	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4535	Phase 3
0.7301	Intermediate Similarity	NPD3787	Discontinued
0.7296	Intermediate Similarity	NPD7819	Suspended
0.7287	Intermediate Similarity	NPD291	Approved
0.7287	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD846	Approved
0.7279	Intermediate Similarity	NPD2238	Phase 2
0.7273	Intermediate Similarity	NPD7473	Discontinued
0.7273	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7240	Approved
0.7256	Intermediate Similarity	NPD2969	Approved
0.7256	Intermediate Similarity	NPD2970	Approved
0.7254	Intermediate Similarity	NPD6582	Phase 2
0.7254	Intermediate Similarity	NPD6583	Phase 3
0.7251	Intermediate Similarity	NPD4663	Approved
0.725	Intermediate Similarity	NPD2560	Approved
0.725	Intermediate Similarity	NPD2563	Approved
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7244	Intermediate Similarity	NPD5403	Approved
0.7241	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6959	Discontinued
0.723	Intermediate Similarity	NPD230	Phase 1
0.7226	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1375	Discontinued
0.7209	Intermediate Similarity	NPD7906	Approved
0.7209	Intermediate Similarity	NPD1242	Phase 1
0.7208	Intermediate Similarity	NPD7124	Phase 2
0.7197	Intermediate Similarity	NPD3686	Approved
0.7197	Intermediate Similarity	NPD3687	Approved
0.7195	Intermediate Similarity	NPD3051	Approved
0.7195	Intermediate Similarity	NPD6071	Discontinued
0.719	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7466	Approved
0.719	Intermediate Similarity	NPD4110	Phase 3
0.7188	Intermediate Similarity	NPD2977	Approved
0.7188	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5773	Approved
0.7188	Intermediate Similarity	NPD2978	Approved
0.7188	Intermediate Similarity	NPD5772	Approved
0.7188	Intermediate Similarity	NPD8455	Phase 2
0.7183	Intermediate Similarity	NPD2231	Phase 2
0.7183	Intermediate Similarity	NPD2235	Phase 2
0.7179	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4578	Approved
0.7176	Intermediate Similarity	NPD7311	Approved
0.7176	Intermediate Similarity	NPD7312	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