NPASS Compound

Structure

NPC147224 OpenBabel07101719252D 39 42 0 0 1 0 0 0 0 0999 V2000 -3.4263 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 7.7942 0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 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 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 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 -2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9921 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 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 -0.0000 -0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 9 2 0 0 0 0 8 26 1 0 0 0 0 9 36 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 11 25 1 0 0 0 0 12 37 1 0 0 0 0 14 15 2 0 0 0 0 14 34 1 0 0 0 0 15 35 1 0 0 0 0 16 12 1 1 0 0 0 16 19 1 0 0 0 0 16 38 1 0 0 0 0 17 26 1 1 0 0 0 17 27 1 0 0 0 0 18 28 2 0 0 0 0 18 37 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 6 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 23 1 0 0 0 0 21 31 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 6 0 0 0 22 26 1 0 0 0 0 23 38 1 0 0 0 0 23 39 1 1 0 0 0 24 36 1 0 0 0 0 24 39 1 1 0 0 0 25 1 1 6 0 0 0 25 32 1 0 0 0 0 26 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.2
Volume:	522.48
LogP:	0.708
LogD:	0.129
LogS:	-3.471
# Rotatable Bonds:	9
TPSA:	193.83
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	4.858
Fsp3:	0.577
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.08
MDCK Permeability:	7.067705882946029e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.923
20% Bioavailability (F20%):	0.1
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	42.01625442504883%
Volume Distribution (VD):	0.393
Pgp-substrate:	20.580007553100586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.219
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.155
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	1.682
Half-life (T1/2):	0.679

ADMET: Toxicity

hERG Blockers:	0.195
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.142
AMES Toxicity:	0.273
Rat Oral Acute Toxicity:	0.373
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.831
Carcinogencity:	0.885
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.861

Download Data

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

Natural Product: NPC147224

Natural Product ID:	NPC147224
*Common Name:**	6'(3,4-Dimethoxycinnamoyl)Harpagide
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-[[(1R,4aR,5S,7R,7aS)-4a,5,7-trihydroxy-7-methyl-1,5,6,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
Synonyms:	6'(3,4-Dimethoxycinnamoyl)Harpagide
Standard InCHIKey:	RCKNZJXQBTVMJV-YHLASNOOSA-N
Standard InCHI:	InChI=1S/C26H34O13/c1-25(32)11-17(27)26(33)8-9-36-24(22(25)26)39-23-21(31)20(30)19(29)16(38-23)12-37-18(28)7-5-13-4-6-14(34-2)15(10-13)35-3/h4-10,16-17,19-24,27,29-33H,11-12H2,1-3H3/b7-5+/t16-,17+,19-,20+,21-,22+,23+,24-,25-,26+/m1/s1
SMILES:	COc1ccc(cc1OC)/C=C/C(=O)OC[C@H]1O[C@@H](O[C@H]2OC=C[C@]3([C@@H]2[C@](C)(O)C[C@@H]3O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL593634
PubChem CID:	45101503
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO33377	teucrium chamaedris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19674906]

☑ 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	4
Others	3

Activity Type	# Activity
NON-MOLECULAR	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.7	n.a.	PMID[513967]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.0	n.a.	PMID[513967]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	6.5	n.a.	PMID[513967]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10700.0	nM	PMID[513967]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	26500.0	nM	PMID[513967]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	33100.0	nM	PMID[513967]
NPT1	Others	Radical scavenging activity		IC50	>	300000.0	nM	PMID[513967]

☑ 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 NPC147224 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	323
0.1-0.2	1329
0.2-0.3	3229
0.3-0.4	7308
0.4-0.5	10437
0.5-0.6	7917
0.6-0.7	9313
0.7-0.8	2505
0.8-0.85	250
0.85-0.9	67
0.9-0.95	9
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC308178
0.9792	High Similarity	NPC269914
0.9792	High Similarity	NPC478249
0.9658	High Similarity	NPC478241
0.9658	High Similarity	NPC229548
0.9658	High Similarity	NPC89693
0.9507	High Similarity	NPC116104
0.9507	High Similarity	NPC263397
0.9507	High Similarity	NPC237872
0.9507	High Similarity	NPC302286
0.9507	High Similarity	NPC88754
0.9463	High Similarity	NPC478248
0.9404	High Similarity	NPC478265
0.931	High Similarity	NPC37838
0.9306	High Similarity	NPC478240
0.9247	High Similarity	NPC18789
0.9178	High Similarity	NPC474234
0.915	High Similarity	NPC474936
0.9091	High Similarity	NPC49597
0.9085	High Similarity	NPC179914
0.9079	High Similarity	NPC478266
0.9032	High Similarity	NPC476011
0.9032	High Similarity	NPC206815
0.8981	High Similarity	NPC301910
0.8981	High Similarity	NPC130730
0.8966	High Similarity	NPC46644
0.894	High Similarity	NPC203664
0.8924	High Similarity	NPC208818
0.8912	High Similarity	NPC184464
0.8912	High Similarity	NPC251062
0.8912	High Similarity	NPC110063
0.8861	High Similarity	NPC282551
0.8828	High Similarity	NPC226005
0.8819	High Similarity	NPC157554
0.8819	High Similarity	NPC37468
0.8776	High Similarity	NPC140502
0.8766	High Similarity	NPC475484
0.875	High Similarity	NPC21956
0.875	High Similarity	NPC475379
0.8725	High Similarity	NPC476382
0.8725	High Similarity	NPC34927
0.8725	High Similarity	NPC287615
0.8725	High Similarity	NPC216819
0.8725	High Similarity	NPC34587
0.8725	High Similarity	NPC252292
0.8725	High Similarity	NPC262182
0.8725	High Similarity	NPC83743
0.8725	High Similarity	NPC100998
0.8716	High Similarity	NPC186296
0.8716	High Similarity	NPC478239
0.8707	High Similarity	NPC7518
0.8707	High Similarity	NPC154262
0.8707	High Similarity	NPC137501
0.8707	High Similarity	NPC159387
0.8701	High Similarity	NPC478232
0.8699	High Similarity	NPC100389
0.8693	High Similarity	NPC478268
0.8688	High Similarity	NPC286809
0.8684	High Similarity	NPC188393
0.8684	High Similarity	NPC470934
0.8662	High Similarity	NPC138993
0.8658	High Similarity	NPC297342
0.8649	High Similarity	NPC157816
0.8642	High Similarity	NPC470685
0.8639	High Similarity	NPC202700
0.8625	High Similarity	NPC475621
0.8618	High Similarity	NPC478242
0.8609	High Similarity	NPC232992
0.8599	High Similarity	NPC469384
0.8591	High Similarity	NPC475213
0.8591	High Similarity	NPC152796
0.8581	High Similarity	NPC186406
0.8562	High Similarity	NPC117346
0.8562	High Similarity	NPC240592
0.8562	High Similarity	NPC186418
0.8553	High Similarity	NPC201148
0.8553	High Similarity	NPC215095
0.8553	High Similarity	NPC199311
0.8553	High Similarity	NPC28651
0.8553	High Similarity	NPC3460
0.8553	High Similarity	NPC300262
0.8553	High Similarity	NPC80732
0.8553	High Similarity	NPC192763
0.8553	High Similarity	NPC261122
0.8553	High Similarity	NPC210611
0.8543	High Similarity	NPC199928
0.8543	High Similarity	NPC476865
0.8535	High Similarity	NPC286919
0.8535	High Similarity	NPC475663
0.8533	High Similarity	NPC232228
0.8516	High Similarity	NPC469699
0.8503	High Similarity	NPC304152
0.85	High Similarity	NPC109990
0.8497	Intermediate Similarity	NPC94871
0.8497	Intermediate Similarity	NPC306890
0.8497	Intermediate Similarity	NPC476398
0.8497	Intermediate Similarity	NPC283839
0.8497	Intermediate Similarity	NPC96599
0.8497	Intermediate Similarity	NPC259347
0.8497	Intermediate Similarity	NPC478236
0.8497	Intermediate Similarity	NPC90896
0.8497	Intermediate Similarity	NPC470933
0.8497	Intermediate Similarity	NPC476386
0.8497	Intermediate Similarity	NPC478234
0.8497	Intermediate Similarity	NPC106138
0.8497	Intermediate Similarity	NPC473427
0.8497	Intermediate Similarity	NPC471062
0.8493	Intermediate Similarity	NPC55040
0.8483	Intermediate Similarity	NPC25821
0.8483	Intermediate Similarity	NPC254398
0.8483	Intermediate Similarity	NPC6836
0.8477	Intermediate Similarity	NPC476866
0.8477	Intermediate Similarity	NPC476869
0.8477	Intermediate Similarity	NPC476864
0.8477	Intermediate Similarity	NPC476868
0.8472	Intermediate Similarity	NPC254819
0.8471	Intermediate Similarity	NPC11411
0.8456	Intermediate Similarity	NPC472711
0.8452	Intermediate Similarity	NPC194705
0.8446	Intermediate Similarity	NPC328273
0.8446	Intermediate Similarity	NPC321638
0.8446	Intermediate Similarity	NPC321184
0.8446	Intermediate Similarity	NPC171134
0.8442	Intermediate Similarity	NPC69367
0.8442	Intermediate Similarity	NPC257970
0.8442	Intermediate Similarity	NPC470927
0.8438	Intermediate Similarity	NPC145847
0.8431	Intermediate Similarity	NPC96294
0.8425	Intermediate Similarity	NPC35731
0.8425	Intermediate Similarity	NPC471883
0.8425	Intermediate Similarity	NPC470881
0.8414	Intermediate Similarity	NPC473924
0.8414	Intermediate Similarity	NPC473285
0.8414	Intermediate Similarity	NPC252833
0.8411	Intermediate Similarity	NPC129417
0.8411	Intermediate Similarity	NPC283995
0.8411	Intermediate Similarity	NPC470235
0.8411	Intermediate Similarity	NPC296659
0.8411	Intermediate Similarity	NPC202391
0.8411	Intermediate Similarity	NPC84181
0.8411	Intermediate Similarity	NPC292443
0.8411	Intermediate Similarity	NPC476867
0.84	Intermediate Similarity	NPC296643
0.8387	Intermediate Similarity	NPC7145
0.8387	Intermediate Similarity	NPC289021
0.8387	Intermediate Similarity	NPC158546
0.8387	Intermediate Similarity	NPC85192
0.8387	Intermediate Similarity	NPC213197
0.8387	Intermediate Similarity	NPC143480
0.8387	Intermediate Similarity	NPC125823
0.838	Intermediate Similarity	NPC276047
0.838	Intermediate Similarity	NPC267733
0.8378	Intermediate Similarity	NPC476376
0.8377	Intermediate Similarity	NPC111785
0.8367	Intermediate Similarity	NPC476870
0.8366	Intermediate Similarity	NPC473149
0.8366	Intermediate Similarity	NPC41844
0.8366	Intermediate Similarity	NPC52740
0.8365	Intermediate Similarity	NPC478269
0.8354	Intermediate Similarity	NPC228357
0.8345	Intermediate Similarity	NPC219677
0.8345	Intermediate Similarity	NPC248307
0.8345	Intermediate Similarity	NPC475824
0.8345	Intermediate Similarity	NPC65942
0.8344	Intermediate Similarity	NPC185307
0.8344	Intermediate Similarity	NPC477898
0.8344	Intermediate Similarity	NPC470950
0.8344	Intermediate Similarity	NPC46092
0.8333	Intermediate Similarity	NPC289967
0.8333	Intermediate Similarity	NPC472611
0.8333	Intermediate Similarity	NPC477293
0.8333	Intermediate Similarity	NPC470264
0.8333	Intermediate Similarity	NPC307110
0.8333	Intermediate Similarity	NPC229784
0.8333	Intermediate Similarity	NPC477294
0.8333	Intermediate Similarity	NPC295970
0.8333	Intermediate Similarity	NPC248355
0.8333	Intermediate Similarity	NPC134405
0.8333	Intermediate Similarity	NPC472612
0.8333	Intermediate Similarity	NPC166040
0.8333	Intermediate Similarity	NPC476385
0.8323	Intermediate Similarity	NPC476871
0.8323	Intermediate Similarity	NPC158635
0.8323	Intermediate Similarity	NPC229882
0.8323	Intermediate Similarity	NPC114740
0.8322	Intermediate Similarity	NPC89105
0.8322	Intermediate Similarity	NPC64141
0.8322	Intermediate Similarity	NPC68092
0.8322	Intermediate Similarity	NPC476383
0.8322	Intermediate Similarity	NPC472350
0.8322	Intermediate Similarity	NPC81515
0.8322	Intermediate Similarity	NPC156376
0.8322	Intermediate Similarity	NPC197316
0.8312	Intermediate Similarity	NPC478237
0.8312	Intermediate Similarity	NPC93924
0.8311	Intermediate Similarity	NPC177035
0.8311	Intermediate Similarity	NPC52277
0.8311	Intermediate Similarity	NPC199459
0.8302	Intermediate Similarity	NPC226759
0.8302	Intermediate Similarity	NPC187205

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 NPC147224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	795
0.2-0.3	1849
0.3-0.4	2730
0.4-0.5	2015
0.5-0.6	1066
0.6-0.7	394
0.7-0.8	41
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.882	High Similarity	NPD7685	Pre-registration
0.8322	Intermediate Similarity	NPD7266	Discontinued
0.8258	Intermediate Similarity	NPD1653	Approved
0.7697	Intermediate Similarity	NPD6653	Approved
0.7644	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD37	Approved
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.7588	Intermediate Similarity	NPD7228	Approved
0.7576	Intermediate Similarity	NPD4966	Approved
0.7576	Intermediate Similarity	NPD4965	Approved
0.7576	Intermediate Similarity	NPD4967	Phase 2
0.7547	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3705	Approved
0.7516	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD5762	Approved
0.75	Intermediate Similarity	NPD5763	Approved
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7448	Intermediate Similarity	NPD1357	Approved
0.7442	Intermediate Similarity	NPD7054	Approved
0.7415	Intermediate Similarity	NPD1091	Approved
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7472	Approved
0.7384	Intermediate Similarity	NPD3818	Discontinued
0.7378	Intermediate Similarity	NPD7028	Phase 2
0.7368	Intermediate Similarity	NPD3027	Phase 3
0.7338	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3620	Phase 2
0.7314	Intermediate Similarity	NPD7240	Approved
0.7312	Intermediate Similarity	NPD6190	Approved
0.7299	Intermediate Similarity	NPD7074	Phase 3
0.7273	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4140	Approved
0.7216	Intermediate Similarity	NPD7251	Discontinued
0.72	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5735	Approved
0.7159	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7124	Intermediate Similarity	NPD2861	Phase 2
0.7118	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1613	Approved
0.7105	Intermediate Similarity	NPD6362	Approved
0.7089	Intermediate Similarity	NPD7097	Phase 1
0.7081	Intermediate Similarity	NPD1652	Phase 2
0.707	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5124	Phase 1
0.7063	Intermediate Similarity	NPD6005	Phase 3
0.7063	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6004	Phase 3
0.7063	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6002	Phase 3
0.7059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4110	Phase 3
0.7037	Intermediate Similarity	NPD4628	Phase 3
0.7022	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD3817	Phase 2
0.6993	Remote Similarity	NPD3094	Phase 2
0.6972	Remote Similarity	NPD1358	Approved
0.6962	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD5536	Phase 2
0.6951	Remote Similarity	NPD5058	Phase 3
0.6949	Remote Similarity	NPD5844	Phase 1
0.6948	Remote Similarity	NPD5647	Approved
0.6944	Remote Similarity	NPD8312	Approved
0.6944	Remote Similarity	NPD8313	Approved
0.6928	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD7095	Approved
0.6918	Remote Similarity	NPD5283	Phase 1
0.6901	Remote Similarity	NPD3134	Approved
0.6899	Remote Similarity	NPD4060	Phase 1
0.6897	Remote Similarity	NPD228	Approved
0.6889	Remote Similarity	NPD7549	Discontinued
0.6885	Remote Similarity	NPD6842	Approved
0.6885	Remote Similarity	NPD6841	Approved
0.6885	Remote Similarity	NPD6843	Phase 3
0.6882	Remote Similarity	NPD1934	Approved
0.6865	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4340	Discontinued
0.6855	Remote Similarity	NPD230	Phase 1
0.6854	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1375	Discontinued
0.6848	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3686	Approved
0.6845	Remote Similarity	NPD3687	Approved
0.6832	Remote Similarity	NPD7033	Discontinued
0.6829	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7157	Approved
0.6813	Remote Similarity	NPD6353	Approved
0.6802	Remote Similarity	NPD5353	Approved
0.6795	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5736	Approved
0.678	Remote Similarity	NPD6166	Phase 2
0.678	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3496	Discontinued
0.6771	Remote Similarity	NPD7680	Approved
0.6766	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4380	Phase 2
0.6753	Remote Similarity	NPD5327	Phase 3
0.6753	Remote Similarity	NPD2982	Phase 2
0.6753	Remote Similarity	NPD2983	Phase 2
0.675	Remote Similarity	NPD1933	Approved
0.675	Remote Similarity	NPD3657	Discovery
0.675	Remote Similarity	NPD447	Suspended
0.6744	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2977	Approved
0.6744	Remote Similarity	NPD2801	Approved
0.6744	Remote Similarity	NPD2978	Approved
0.6742	Remote Similarity	NPD7473	Discontinued
0.6735	Remote Similarity	NPD7843	Approved
0.6732	Remote Similarity	NPD422	Phase 1
0.6732	Remote Similarity	NPD3092	Approved
0.6731	Remote Similarity	NPD4624	Approved
0.673	Remote Similarity	NPD6233	Phase 2
0.6727	Remote Similarity	NPD8166	Discontinued
0.6724	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7075	Discontinued
0.6721	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4626	Approved
0.6708	Remote Similarity	NPD2492	Phase 1
0.6707	Remote Similarity	NPD4357	Discontinued
0.6707	Remote Similarity	NPD2424	Discontinued
0.6706	Remote Similarity	NPD7458	Discontinued
0.6705	Remote Similarity	NPD5402	Approved
0.6704	Remote Similarity	NPD7799	Discontinued
0.6704	Remote Similarity	NPD3751	Discontinued
0.6688	Remote Similarity	NPD2981	Phase 2
0.6688	Remote Similarity	NPD3018	Phase 2
0.6688	Remote Similarity	NPD9494	Approved
0.6685	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7296	Approved
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD4237	Approved
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4236	Phase 3
0.6667	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD969	Suspended
0.6667	Remote Similarity	NPD3882	Suspended
0.6648	Remote Similarity	NPD5494	Approved
0.6647	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7819	Suspended
0.6647	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1465	Phase 2
0.6646	Remote Similarity	NPD4908	Phase 1
0.6645	Remote Similarity	NPD5691	Approved
0.6628	Remote Similarity	NPD6385	Approved
0.6628	Remote Similarity	NPD6386	Approved
0.6627	Remote Similarity	NPD6331	Phase 2
0.6627	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4108	Discontinued
0.6625	Remote Similarity	NPD6663	Approved
0.6624	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD8651	Approved
0.6601	Remote Similarity	NPD5126	Approved
0.6601	Remote Similarity	NPD5125	Phase 3
0.6598	Remote Similarity	NPD7497	Discontinued
0.659	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6801	Discontinued
0.6588	Remote Similarity	NPD5403	Approved
0.6584	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2684	Approved
0.6573	Remote Similarity	NPD3787	Discontinued
0.6564	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4538	Approved
0.6564	Remote Similarity	NPD4536	Approved
0.6564	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6798	Discontinued
0.6561	Remote Similarity	NPD2797	Approved
0.6559	Remote Similarity	NPD8434	Phase 2
0.6557	Remote Similarity	NPD7039	Approved
0.6557	Remote Similarity	NPD7038	Approved
0.6552	Remote Similarity	NPD5760	Phase 2
0.6552	Remote Similarity	NPD5773	Approved
0.6552	Remote Similarity	NPD5772	Approved
0.6552	Remote Similarity	NPD5761	Phase 2
0.655	Remote Similarity	NPD4210	Discontinued
0.6538	Remote Similarity	NPD4749	Approved
0.6536	Remote Similarity	NPD5585	Approved
0.6531	Remote Similarity	NPD7999	Approved
0.6524	Remote Similarity	NPD5588	Approved
0.6522	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7930	Approved
0.6516	Remote Similarity	NPD1610	Phase 2
0.6513	Remote Similarity	NPD7435	Discontinued
0.6512	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1511	Approved
0.6507	Remote Similarity	NPD290	Approved
0.6497	Remote Similarity	NPD3225	Approved
0.6494	Remote Similarity	NPD1778	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