NPASS Compound

Structure

NPC61946 OpenBabel07101718202D 23 25 0 0 1 0 0 0 0 0999 V2000 -5.1962 -1.0000 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 -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 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 2 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 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 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -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 4 2 0 0 0 0 3 9 1 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 16 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 7 15 2 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 6 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 16 22 1 0 0 0 0 17 9 1 6 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.11
Volume:	313.841
LogP:	1.951
LogD:	2.334
LogS:	-2.735
# Rotatable Bonds:	3
TPSA:	88.38
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.804
Synthetic Accessibility Score:	3.108
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.447
MDCK Permeability:	7.204249868664192e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.091
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	92.45718383789062%
Volume Distribution (VD):	0.926
Pgp-substrate:	8.836076736450195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.233
CYP1A2-substrate:	0.763
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.49
CYP2C9-inhibitor:	0.311
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.292
CYP2D6-substrate:	0.779
CYP3A4-inhibitor:	0.689
CYP3A4-substrate:	0.585

ADMET: Excretion

Clearance (CL):	12.265
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.238
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.275
Skin Sensitization:	0.661
Carcinogencity:	0.127
Eye Corrosion:	0.003
Eye Irritation:	0.135
Respiratory Toxicity:	0.541

Download Data

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

Natural Product: NPC61946

Natural Product ID:	NPC61946
*Common Name:**	3',4'-Di-O-Methyl-(-)-Epicatechin
IUPAC Name:	(2R,3R)-2-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms:
Standard InCHIKey:	INGGXWWOTDZRPX-CXAGYDPISA-N
Standard InCHI:	InChI=1S/C17H18O6/c1-21-14-4-3-9(5-16(14)22-2)17-13(20)8-11-12(19)6-10(18)7-15(11)23-17/h3-7,13,17-20H,8H2,1-2H3/t13-,17-/m1/s1
SMILES:	COc1ccc(cc1OC)[C@@H]1[C@@H](Cc2c(cc(cc2O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485663
PubChem CID:	14732293
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
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO14242	Maytenus laevis	Species	Celastraceae	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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	198.6	pg/ml	PMID[558978]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	473.4	pg/ml	PMID[558978]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[558978]

☑ 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 NPC61946 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	417
0.1-0.2	1584
0.2-0.3	4764
0.3-0.4	12195
0.4-0.5	5691
0.5-0.6	3938
0.6-0.7	5872
0.7-0.8	6059
0.8-0.85	1140
0.85-0.9	681
0.9-0.95	283
0.95-1	73

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC306441
0.9922	High Similarity	NPC16435
0.9845	High Similarity	NPC112246
0.9845	High Similarity	NPC470356
0.9845	High Similarity	NPC94750
0.9845	High Similarity	NPC112939
0.9845	High Similarity	NPC121812
0.9845	High Similarity	NPC234333
0.9845	High Similarity	NPC47398
0.9845	High Similarity	NPC260898
0.9845	High Similarity	NPC474206
0.9844	High Similarity	NPC263064
0.9769	High Similarity	NPC269091
0.9769	High Similarity	NPC474639
0.9769	High Similarity	NPC302701
0.9769	High Similarity	NPC227503
0.9769	High Similarity	NPC230734
0.9695	High Similarity	NPC102904
0.9695	High Similarity	NPC326797
0.9695	High Similarity	NPC103976
0.9695	High Similarity	NPC474282
0.9695	High Similarity	NPC211549
0.9695	High Similarity	NPC107551
0.9695	High Similarity	NPC176051
0.9692	High Similarity	NPC151224
0.9692	High Similarity	NPC164787
0.969	High Similarity	NPC475840
0.969	High Similarity	NPC11060
0.9624	High Similarity	NPC471389
0.9621	High Similarity	NPC471388
0.9618	High Similarity	NPC265433
0.9618	High Similarity	NPC472336
0.9618	High Similarity	NPC162659
0.9618	High Similarity	NPC270456
0.9618	High Similarity	NPC470802
0.9618	High Similarity	NPC248727
0.9618	High Similarity	NPC472334
0.9615	High Similarity	NPC317380
0.9615	High Similarity	NPC170694
0.9612	High Similarity	NPC78770
0.9612	High Similarity	NPC253105
0.9612	High Similarity	NPC86655
0.9612	High Similarity	NPC202762
0.9612	High Similarity	NPC127624
0.9612	High Similarity	NPC201587
0.9612	High Similarity	NPC185604
0.9612	High Similarity	NPC15658
0.9612	High Similarity	NPC126029
0.9612	High Similarity	NPC261619
0.9612	High Similarity	NPC61477
0.9612	High Similarity	NPC219876
0.9549	High Similarity	NPC184797
0.9549	High Similarity	NPC309124
0.9545	High Similarity	NPC276490
0.9542	High Similarity	NPC195022
0.9542	High Similarity	NPC472337
0.9542	High Similarity	NPC473413
0.9538	High Similarity	NPC168059
0.9538	High Similarity	NPC229442
0.9535	High Similarity	NPC268266
0.9535	High Similarity	NPC268342
0.9535	High Similarity	NPC220825
0.9535	High Similarity	NPC472597
0.9535	High Similarity	NPC42760
0.9531	High Similarity	NPC470258
0.9531	High Similarity	NPC190629
0.9531	High Similarity	NPC285339
0.9531	High Similarity	NPC226788
0.9531	High Similarity	NPC273295
0.9531	High Similarity	NPC218856
0.9531	High Similarity	NPC202582
0.9531	High Similarity	NPC222004
0.9531	High Similarity	NPC210623
0.9531	High Similarity	NPC3439
0.9474	High Similarity	NPC319647
0.9474	High Similarity	NPC245207
0.9474	High Similarity	NPC473739
0.9474	High Similarity	NPC70682
0.9474	High Similarity	NPC232164
0.9474	High Similarity	NPC25966
0.9474	High Similarity	NPC260741
0.9474	High Similarity	NPC236306
0.9474	High Similarity	NPC127218
0.947	High Similarity	NPC173660
0.947	High Similarity	NPC234952
0.9466	High Similarity	NPC478085
0.9462	High Similarity	NPC35932
0.9462	High Similarity	NPC7903
0.9462	High Similarity	NPC470752
0.9462	High Similarity	NPC16208
0.9462	High Similarity	NPC160991
0.9462	High Similarity	NPC184447
0.9457	High Similarity	NPC472338
0.9453	High Similarity	NPC31707
0.9407	High Similarity	NPC107161
0.9403	High Similarity	NPC22317
0.9403	High Similarity	NPC27495
0.9385	High Similarity	NPC103799
0.9385	High Similarity	NPC30043
0.9385	High Similarity	NPC469613
0.9385	High Similarity	NPC469625
0.9385	High Similarity	NPC309787
0.938	High Similarity	NPC86030
0.938	High Similarity	NPC5851
0.938	High Similarity	NPC212015
0.938	High Similarity	NPC476968
0.938	High Similarity	NPC170844
0.938	High Similarity	NPC469963
0.938	High Similarity	NPC469951
0.9375	High Similarity	NPC474119
0.9375	High Similarity	NPC242032
0.9343	High Similarity	NPC475096
0.9338	High Similarity	NPC81638
0.9333	High Similarity	NPC35216
0.9333	High Similarity	NPC263261
0.9333	High Similarity	NPC247291
0.9333	High Similarity	NPC87725
0.9333	High Similarity	NPC178054
0.9328	High Similarity	NPC22517
0.9328	High Similarity	NPC32630
0.9318	High Similarity	NPC310854
0.9318	High Similarity	NPC106215
0.9308	High Similarity	NPC469614
0.9308	High Similarity	NPC469612
0.9308	High Similarity	NPC91291
0.9302	High Similarity	NPC470213
0.9302	High Similarity	NPC252307
0.9302	High Similarity	NPC206615
0.9302	High Similarity	NPC87224
0.9302	High Similarity	NPC474178
0.9302	High Similarity	NPC98631
0.9302	High Similarity	NPC186843
0.9302	High Similarity	NPC222572
0.9302	High Similarity	NPC226331
0.9302	High Similarity	NPC72529
0.9302	High Similarity	NPC46274
0.9302	High Similarity	NPC245826
0.9275	High Similarity	NPC125755
0.9275	High Similarity	NPC99515
0.9275	High Similarity	NPC190714
0.927	High Similarity	NPC171932
0.927	High Similarity	NPC12641
0.927	High Similarity	NPC280092
0.927	High Similarity	NPC50250
0.927	High Similarity	NPC45257
0.927	High Similarity	NPC93323
0.927	High Similarity	NPC473108
0.927	High Similarity	NPC28440
0.9265	High Similarity	NPC475891
0.9265	High Similarity	NPC204347
0.9265	High Similarity	NPC475084
0.9265	High Similarity	NPC189115
0.9265	High Similarity	NPC59841
0.9265	High Similarity	NPC2613
0.9259	High Similarity	NPC259519
0.9259	High Similarity	NPC266197
0.9259	High Similarity	NPC160283
0.9259	High Similarity	NPC254759
0.9259	High Similarity	NPC291101
0.9254	High Similarity	NPC474390
0.9254	High Similarity	NPC477938
0.9248	High Similarity	NPC134968
0.9248	High Similarity	NPC256262
0.9237	High Similarity	NPC470095
0.9237	High Similarity	NPC474017
0.9237	High Similarity	NPC470096
0.9225	High Similarity	NPC236791
0.9225	High Similarity	NPC293054
0.9225	High Similarity	NPC324112
0.9225	High Similarity	NPC250432
0.9225	High Similarity	NPC111247
0.9225	High Similarity	NPC147821
0.9225	High Similarity	NPC169474
0.9225	High Similarity	NPC183181
0.9225	High Similarity	NPC319625
0.9225	High Similarity	NPC163332
0.9225	High Similarity	NPC74817
0.9225	High Similarity	NPC5447
0.9225	High Similarity	NPC82679
0.9225	High Similarity	NPC292056
0.9225	High Similarity	NPC124452
0.9225	High Similarity	NPC246620
0.9225	High Similarity	NPC159968
0.9225	High Similarity	NPC118787
0.9225	High Similarity	NPC282000
0.9225	High Similarity	NPC210355
0.9225	High Similarity	NPC41706
0.9219	High Similarity	NPC167571
0.9219	High Similarity	NPC278552
0.9219	High Similarity	NPC207179
0.9219	High Similarity	NPC105925
0.9209	High Similarity	NPC474397
0.9209	High Similarity	NPC227902
0.9203	High Similarity	NPC277867
0.9203	High Similarity	NPC161700
0.9197	High Similarity	NPC85264
0.9197	High Similarity	NPC47633
0.9197	High Similarity	NPC477616
0.9197	High Similarity	NPC102044
0.9191	High Similarity	NPC265075

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 NPC61946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	876
0.2-0.3	1916
0.3-0.4	2682
0.4-0.5	1555
0.5-0.6	882
0.6-0.7	667
0.7-0.8	185
0.8-0.85	13
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9612	High Similarity	NPD1612	Clinical (unspecified phase)
0.9612	High Similarity	NPD1613	Approved
0.938	High Similarity	NPD3027	Phase 3
0.9302	High Similarity	NPD1529	Clinical (unspecified phase)
0.9225	High Similarity	NPD1530	Clinical (unspecified phase)
0.8722	High Similarity	NPD4908	Phase 1
0.8615	High Similarity	NPD1610	Phase 2
0.8593	High Similarity	NPD4907	Clinical (unspecified phase)
0.8571	High Similarity	NPD1934	Approved
0.845	Intermediate Similarity	NPD1548	Phase 1
0.8389	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD2861	Phase 2
0.8299	Intermediate Similarity	NPD1653	Approved
0.8258	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6166	Phase 2
0.8248	Intermediate Similarity	NPD4625	Phase 3
0.8235	Intermediate Similarity	NPD3018	Phase 2
0.8209	Intermediate Similarity	NPD4749	Approved
0.8188	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD2801	Approved
0.8125	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD2982	Phase 2
0.8074	Intermediate Similarity	NPD2983	Phase 2
0.806	Intermediate Similarity	NPD1091	Approved
0.805	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD2981	Phase 2
0.8	Intermediate Similarity	NPD6674	Discontinued
0.7987	Intermediate Similarity	NPD7054	Approved
0.7937	Intermediate Similarity	NPD7472	Approved
0.7925	Intermediate Similarity	NPD3818	Discontinued
0.7923	Intermediate Similarity	NPD5283	Phase 1
0.7922	Intermediate Similarity	NPD3882	Suspended
0.7907	Intermediate Similarity	NPD228	Approved
0.7905	Intermediate Similarity	NPD1511	Approved
0.7902	Intermediate Similarity	NPD4538	Approved
0.7902	Intermediate Similarity	NPD4536	Approved
0.7902	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1652	Phase 2
0.7875	Intermediate Similarity	NPD5844	Phase 1
0.7857	Intermediate Similarity	NPD3817	Phase 2
0.7843	Intermediate Similarity	NPD37	Approved
0.7834	Intermediate Similarity	NPD7199	Phase 2
0.7829	Intermediate Similarity	NPD4380	Phase 2
0.7821	Intermediate Similarity	NPD6234	Discontinued
0.7817	Intermediate Similarity	NPD4060	Phase 1
0.7812	Intermediate Similarity	NPD2684	Approved
0.7806	Intermediate Similarity	NPD4967	Phase 2
0.7806	Intermediate Similarity	NPD4965	Approved
0.7806	Intermediate Similarity	NPD4966	Approved
0.7803	Intermediate Similarity	NPD6671	Approved
0.7801	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1512	Approved
0.7791	Intermediate Similarity	NPD7808	Phase 3
0.7785	Intermediate Similarity	NPD7212	Phase 2
0.7785	Intermediate Similarity	NPD7213	Phase 3
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7762	Intermediate Similarity	NPD5124	Phase 1
0.7762	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5177	Phase 3
0.7754	Intermediate Similarity	NPD8651	Approved
0.774	Intermediate Similarity	NPD7266	Discontinued
0.774	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD290	Approved
0.7733	Intermediate Similarity	NPD7447	Phase 1
0.773	Intermediate Similarity	NPD7251	Discontinued
0.7724	Intermediate Similarity	NPD5588	Approved
0.7724	Intermediate Similarity	NPD5960	Phase 3
0.7712	Intermediate Similarity	NPD4678	Approved
0.7712	Intermediate Similarity	NPD4675	Approved
0.771	Intermediate Similarity	NPD7843	Approved
0.7702	Intermediate Similarity	NPD7228	Approved
0.7692	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1558	Phase 1
0.7692	Intermediate Similarity	NPD3620	Phase 2
0.7687	Intermediate Similarity	NPD1549	Phase 2
0.7683	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7157	Approved
0.7664	Intermediate Similarity	NPD422	Phase 1
0.7658	Intermediate Similarity	NPD5494	Approved
0.7651	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7075	Discontinued
0.7643	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3540	Phase 1
0.7616	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5058	Phase 3
0.7564	Intermediate Similarity	NPD1465	Phase 2
0.7564	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6798	Discontinued
0.7551	Intermediate Similarity	NPD6099	Approved
0.7551	Intermediate Similarity	NPD3539	Phase 1
0.7551	Intermediate Similarity	NPD6100	Approved
0.7536	Intermediate Similarity	NPD3705	Approved
0.7533	Intermediate Similarity	NPD2677	Approved
0.7532	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4005	Discontinued
0.7518	Intermediate Similarity	NPD5846	Approved
0.7518	Intermediate Similarity	NPD6584	Phase 3
0.7518	Intermediate Similarity	NPD6516	Phase 2
0.7517	Intermediate Similarity	NPD3060	Approved
0.7515	Intermediate Similarity	NPD6559	Discontinued
0.7483	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3022	Approved
0.7481	Intermediate Similarity	NPD3021	Approved
0.747	Intermediate Similarity	NPD7549	Discontinued
0.7467	Intermediate Similarity	NPD3892	Phase 2
0.7453	Intermediate Similarity	NPD6232	Discontinued
0.7451	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2424	Discontinued
0.7445	Intermediate Similarity	NPD1357	Approved
0.7439	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1774	Approved
0.7432	Intermediate Similarity	NPD2796	Approved
0.7429	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5402	Approved
0.7405	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4162	Approved
0.74	Intermediate Similarity	NPD4236	Phase 3
0.74	Intermediate Similarity	NPD4237	Approved
0.7397	Intermediate Similarity	NPD6355	Discontinued
0.7397	Intermediate Similarity	NPD5735	Approved
0.7389	Intermediate Similarity	NPD6801	Discontinued
0.7386	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4123	Phase 3
0.7385	Intermediate Similarity	NPD968	Approved
0.7383	Intermediate Similarity	NPD5763	Approved
0.7383	Intermediate Similarity	NPD5762	Approved
0.7381	Intermediate Similarity	NPD8054	Approved
0.7381	Intermediate Similarity	NPD8053	Approved
0.7379	Intermediate Similarity	NPD6233	Phase 2
0.7365	Intermediate Similarity	NPD1510	Phase 2
0.7365	Intermediate Similarity	NPD7033	Discontinued
0.7361	Intermediate Similarity	NPD7095	Approved
0.7351	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3750	Approved
0.7351	Intermediate Similarity	NPD4535	Phase 3
0.7351	Intermediate Similarity	NPD6331	Phase 2
0.7351	Intermediate Similarity	NPD4628	Phase 3
0.7346	Intermediate Similarity	NPD3787	Discontinued
0.7344	Intermediate Similarity	NPD940	Approved
0.7344	Intermediate Similarity	NPD846	Approved
0.7344	Intermediate Similarity	NPD291	Approved
0.7342	Intermediate Similarity	NPD7819	Suspended
0.7329	Intermediate Similarity	NPD2238	Phase 2
0.732	Intermediate Similarity	NPD4357	Discontinued
0.732	Intermediate Similarity	NPD6799	Approved
0.732	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7473	Discontinued
0.7305	Intermediate Similarity	NPD6583	Phase 3
0.7305	Intermediate Similarity	NPD6582	Phase 2
0.7305	Intermediate Similarity	NPD7240	Approved
0.7303	Intermediate Similarity	NPD6190	Approved
0.7301	Intermediate Similarity	NPD2970	Approved
0.7301	Intermediate Similarity	NPD2969	Approved
0.7299	Intermediate Similarity	NPD5536	Phase 2
0.7296	Intermediate Similarity	NPD2560	Approved
0.7296	Intermediate Similarity	NPD2563	Approved
0.7292	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5403	Approved
0.7284	Intermediate Similarity	NPD6959	Discontinued
0.7267	Intermediate Similarity	NPD1375	Discontinued
0.7266	Intermediate Similarity	NPD1242	Phase 1
0.7256	Intermediate Similarity	NPD27	Approved
0.7256	Intermediate Similarity	NPD2489	Approved
0.7255	Intermediate Similarity	NPD7124	Phase 2
0.7244	Intermediate Similarity	NPD3687	Approved
0.7244	Intermediate Similarity	NPD3686	Approved
0.7239	Intermediate Similarity	NPD3051	Approved
0.7239	Intermediate Similarity	NPD6071	Discontinued
0.7237	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7466	Approved
0.7237	Intermediate Similarity	NPD4110	Phase 3
0.7234	Intermediate Similarity	NPD2231	Phase 2
0.7234	Intermediate Similarity	NPD2235	Phase 2
0.7233	Intermediate Similarity	NPD8455	Phase 2
0.7233	Intermediate Similarity	NPD5773	Approved
0.7233	Intermediate Similarity	NPD5772	Approved
0.7233	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD4750	Phase 3
0.7215	Intermediate Similarity	NPD7411	Suspended
0.7214	Intermediate Similarity	NPD3496	Discontinued
0.7211	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1240	Approved
0.72	Intermediate Similarity	NPD6032	Approved
0.7193	Intermediate Similarity	NPD4663	Approved
0.719	Intermediate Similarity	NPD2219	Phase 1
0.7185	Intermediate Similarity	NPD5535	Approved
0.7181	Intermediate Similarity	NPD7097	Phase 1

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