NPASS Compound

Structure

NPC24257 OpenBabel07101718302D 28 30 0 0 1 0 0 0 0 0999 V2000 4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 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 4.4152 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 13 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 26 1 0 0 0 0 11 27 1 0 0 0 0 12 1 1 6 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 22 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 6 0 0 0 21 23 2 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.14
Volume:	386.543
LogP:	3.198
LogD:	3.087
LogS:	-4.935
# Rotatable Bonds:	8
TPSA:	80.29
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	3.057
Fsp3:	0.333
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:	-4.751
MDCK Permeability:	6.206968828337267e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.103

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	98.280029296875%
Volume Distribution (VD):	0.625
Pgp-substrate:	3.1189422607421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.606
CYP1A2-substrate:	0.92
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.657
CYP2C9-inhibitor:	0.917
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.951
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.744

ADMET: Excretion

Clearance (CL):	11.303
Half-life (T1/2):	0.57

ADMET: Toxicity

hERG Blockers:	0.119
Human Hepatotoxicity (H-HT):	0.247
Drug-inuced Liver Injury (DILI):	0.904
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.148
Carcinogencity:	0.602
Eye Corrosion:	0.004
Eye Irritation:	0.056
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC24257

Natural Product ID:	NPC24257
*Common Name:**	(7'r,8's)-3,4-Methylenedioxy-3',4'-Dimethoxy-7,8-Seco-7,7'-Epoxylignan-7,8-Dione
IUPAC Name:	[(1R,2S)-1-(3,4-dimethoxyphenyl)-2-methyl-3-oxobutyl] 1,3-benzodioxole-5-carboxylate
Synonyms:
Standard InCHIKey:	JTXRNQSIUILDTQ-MPBGBICISA-N
Standard InCHI:	InChI=1S/C21H22O7/c1-12(13(2)22)20(14-5-7-16(24-3)18(9-14)25-4)28-21(23)15-6-8-17-19(10-15)27-11-26-17/h5-10,12,20H,11H2,1-4H3/t12-,20-/m1/s1
SMILES:	COc1cc(ccc1OC)[C@@H]([C@@H](C(=O)C)C)OC(=O)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3290505
PubChem CID:	90682208
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001097] Benzyloxycarbonyls

*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
NPO19979	Schisandra glaucescens	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[23373215]
NPO19979	Schisandra glaucescens	Species	Schisandraceae	Eukaryota	fruit	n.a.	n.a.	PMID[24927000]
NPO19979	Schisandra glaucescens	Species	Schisandraceae	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	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	53.2	%	PMID[548407]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	62.0	%	PMID[548407]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	63.5	%	PMID[548407]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	63.4	%	PMID[548407]

☑ 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 NPC24257 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	381
0.1-0.2	1459
0.2-0.3	3517
0.3-0.4	7981
0.4-0.5	10372
0.5-0.6	3993
0.6-0.7	6482
0.7-0.8	7919
0.8-0.85	505
0.85-0.9	80
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC153620
0.9586	High Similarity	NPC308555
0.9456	High Similarity	NPC254163
0.9103	High Similarity	NPC213482
0.9103	High Similarity	NPC30890
0.9079	High Similarity	NPC239818
0.9079	High Similarity	NPC218471
0.9021	High Similarity	NPC51681
0.9007	High Similarity	NPC261484
0.8966	High Similarity	NPC15743
0.8904	High Similarity	NPC327052
0.8889	High Similarity	NPC325122
0.8882	High Similarity	NPC301897
0.8874	High Similarity	NPC478213
0.8844	High Similarity	NPC296575
0.8844	High Similarity	NPC224687
0.8831	High Similarity	NPC139876
0.8824	High Similarity	NPC82733
0.8824	High Similarity	NPC76458
0.8824	High Similarity	NPC258644
0.8808	High Similarity	NPC137813
0.8808	High Similarity	NPC148497
0.8808	High Similarity	NPC153008
0.8808	High Similarity	NPC68882
0.88	High Similarity	NPC62354
0.8774	High Similarity	NPC209411
0.8774	High Similarity	NPC239890
0.8767	High Similarity	NPC137920
0.8767	High Similarity	NPC125134
0.8767	High Similarity	NPC86455
0.8766	High Similarity	NPC68619
0.8766	High Similarity	NPC15764
0.8759	High Similarity	NPC28398
0.8758	High Similarity	NPC155063
0.875	High Similarity	NPC57211
0.8742	High Similarity	NPC279061
0.8742	High Similarity	NPC151425
0.8741	High Similarity	NPC230968
0.8741	High Similarity	NPC102260
0.8718	High Similarity	NPC478199
0.8718	High Similarity	NPC61141
0.8718	High Similarity	NPC76687
0.8707	High Similarity	NPC46880
0.8707	High Similarity	NPC473090
0.8701	High Similarity	NPC226759
0.8693	High Similarity	NPC10205
0.8693	High Similarity	NPC478238
0.8684	High Similarity	NPC52623
0.8675	High Similarity	NPC243891
0.8662	High Similarity	NPC205915
0.8654	High Similarity	NPC296540
0.8654	High Similarity	NPC309335
0.8654	High Similarity	NPC34376
0.8649	High Similarity	NPC474158
0.8636	High Similarity	NPC477380
0.8636	High Similarity	NPC471405
0.8633	High Similarity	NPC286683
0.8627	High Similarity	NPC244371
0.8627	High Similarity	NPC25127
0.8618	High Similarity	NPC134905
0.8618	High Similarity	NPC267091
0.8618	High Similarity	NPC36130
0.8618	High Similarity	NPC118332
0.8618	High Similarity	NPC220577
0.8608	High Similarity	NPC475738
0.8608	High Similarity	NPC474301
0.8608	High Similarity	NPC477884
0.8601	High Similarity	NPC311339
0.8601	High Similarity	NPC45404
0.8601	High Similarity	NPC37065
0.8599	High Similarity	NPC19948
0.8581	High Similarity	NPC475000
0.8581	High Similarity	NPC46161
0.8581	High Similarity	NPC474036
0.8581	High Similarity	NPC477885
0.8581	High Similarity	NPC239608
0.8581	High Similarity	NPC310206
0.8571	High Similarity	NPC3273
0.8571	High Similarity	NPC176586
0.8571	High Similarity	NPC210354
0.8571	High Similarity	NPC284353
0.8562	High Similarity	NPC292460
0.8561	High Similarity	NPC154275
0.8553	High Similarity	NPC234152
0.8552	High Similarity	NPC14022
0.8552	High Similarity	NPC166184
0.8544	High Similarity	NPC100425
0.8544	High Similarity	NPC100420
0.8526	High Similarity	NPC76211
0.8526	High Similarity	NPC113055
0.8526	High Similarity	NPC62518
0.8526	High Similarity	NPC215375
0.8519	High Similarity	NPC477881
0.8516	High Similarity	NPC261090
0.8506	High Similarity	NPC327032
0.8506	High Similarity	NPC191046
0.8506	High Similarity	NPC279930
0.8506	High Similarity	NPC194095
0.8506	High Similarity	NPC186507
0.8506	High Similarity	NPC287504
0.85	High Similarity	NPC223807
0.8497	Intermediate Similarity	NPC56184
0.8497	Intermediate Similarity	NPC104353
0.8491	Intermediate Similarity	NPC180586
0.8487	Intermediate Similarity	NPC12854
0.8481	Intermediate Similarity	NPC273021
0.8481	Intermediate Similarity	NPC125991
0.8481	Intermediate Similarity	NPC18284
0.8477	Intermediate Similarity	NPC472969
0.8472	Intermediate Similarity	NPC19890
0.8472	Intermediate Similarity	NPC110958
0.8471	Intermediate Similarity	NPC78944
0.8467	Intermediate Similarity	NPC193779
0.8467	Intermediate Similarity	NPC3982
0.8462	Intermediate Similarity	NPC472860
0.8462	Intermediate Similarity	NPC167595
0.8462	Intermediate Similarity	NPC474990
0.8456	Intermediate Similarity	NPC191158
0.8456	Intermediate Similarity	NPC177644
0.8456	Intermediate Similarity	NPC469615
0.8446	Intermediate Similarity	NPC40237
0.8446	Intermediate Similarity	NPC151423
0.8442	Intermediate Similarity	NPC104728
0.8442	Intermediate Similarity	NPC157898
0.8442	Intermediate Similarity	NPC35544
0.8442	Intermediate Similarity	NPC44730
0.8421	Intermediate Similarity	NPC476394
0.8421	Intermediate Similarity	NPC111785
0.8421	Intermediate Similarity	NPC477698
0.8421	Intermediate Similarity	NPC98809
0.8421	Intermediate Similarity	NPC127827
0.8418	Intermediate Similarity	NPC260640
0.8418	Intermediate Similarity	NPC295009
0.8418	Intermediate Similarity	NPC258322
0.8418	Intermediate Similarity	NPC191352
0.8418	Intermediate Similarity	NPC99968
0.8418	Intermediate Similarity	NPC319749
0.8414	Intermediate Similarity	NPC211386
0.8411	Intermediate Similarity	NPC216314
0.8411	Intermediate Similarity	NPC120924
0.8411	Intermediate Similarity	NPC195919
0.8411	Intermediate Similarity	NPC25496
0.8408	Intermediate Similarity	NPC104459
0.8408	Intermediate Similarity	NPC125713
0.8408	Intermediate Similarity	NPC257914
0.8408	Intermediate Similarity	NPC238405
0.8405	Intermediate Similarity	NPC474568
0.8403	Intermediate Similarity	NPC288743
0.84	Intermediate Similarity	NPC223185
0.84	Intermediate Similarity	NPC213900
0.84	Intermediate Similarity	NPC184702
0.84	Intermediate Similarity	NPC229787
0.84	Intermediate Similarity	NPC469683
0.84	Intermediate Similarity	NPC470932
0.84	Intermediate Similarity	NPC27106
0.8397	Intermediate Similarity	NPC239113
0.8397	Intermediate Similarity	NPC109765
0.8397	Intermediate Similarity	NPC115123
0.8395	Intermediate Similarity	NPC477883
0.8395	Intermediate Similarity	NPC212748
0.8389	Intermediate Similarity	NPC474288
0.8389	Intermediate Similarity	NPC28326
0.8389	Intermediate Similarity	NPC185607
0.8387	Intermediate Similarity	NPC476364
0.8387	Intermediate Similarity	NPC178195
0.8387	Intermediate Similarity	NPC348849
0.8385	Intermediate Similarity	NPC116745
0.8385	Intermediate Similarity	NPC471180
0.8378	Intermediate Similarity	NPC326065
0.8377	Intermediate Similarity	NPC473732
0.8367	Intermediate Similarity	NPC233780
0.8367	Intermediate Similarity	NPC470962
0.8367	Intermediate Similarity	NPC44573
0.8366	Intermediate Similarity	NPC473091
0.8366	Intermediate Similarity	NPC475722
0.8366	Intermediate Similarity	NPC227980
0.8366	Intermediate Similarity	NPC158635
0.8366	Intermediate Similarity	NPC474648
0.8366	Intermediate Similarity	NPC205054
0.8366	Intermediate Similarity	NPC229882
0.8366	Intermediate Similarity	NPC238366
0.8365	Intermediate Similarity	NPC280778
0.8365	Intermediate Similarity	NPC469575
0.8365	Intermediate Similarity	NPC414831
0.8365	Intermediate Similarity	NPC302741
0.8364	Intermediate Similarity	NPC477880
0.8364	Intermediate Similarity	NPC477882
0.8356	Intermediate Similarity	NPC90431
0.8356	Intermediate Similarity	NPC77955
0.8355	Intermediate Similarity	NPC473428
0.8355	Intermediate Similarity	NPC1580
0.8355	Intermediate Similarity	NPC117463
0.8355	Intermediate Similarity	NPC470511
0.8354	Intermediate Similarity	NPC203020
0.8354	Intermediate Similarity	NPC298093
0.8354	Intermediate Similarity	NPC285973
0.8354	Intermediate Similarity	NPC474770
0.8354	Intermediate Similarity	NPC225624
0.8354	Intermediate Similarity	NPC43971
0.8354	Intermediate Similarity	NPC19554

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 NPC24257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	880
0.2-0.3	1643
0.3-0.4	2604
0.4-0.5	1917
0.5-0.6	1113
0.6-0.7	515
0.7-0.8	152
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8851	High Similarity	NPD6980	Clinical (unspecified phase)
0.8649	High Similarity	NPD6143	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD3818	Discontinued
0.8354	Intermediate Similarity	NPD5494	Approved
0.8141	Intermediate Similarity	NPD6385	Approved
0.8141	Intermediate Similarity	NPD6386	Approved
0.8101	Intermediate Similarity	NPD3817	Phase 2
0.805	Intermediate Similarity	NPD3882	Suspended
0.7975	Intermediate Similarity	NPD1934	Approved
0.7975	Intermediate Similarity	NPD37	Approved
0.7964	Intermediate Similarity	NPD7685	Pre-registration
0.7961	Intermediate Similarity	NPD4628	Phase 3
0.7952	Intermediate Similarity	NPD7074	Phase 3
0.795	Intermediate Similarity	NPD919	Approved
0.7937	Intermediate Similarity	NPD4966	Approved
0.7937	Intermediate Similarity	NPD4965	Approved
0.7937	Intermediate Similarity	NPD4967	Phase 2
0.7917	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1933	Approved
0.7892	Intermediate Similarity	NPD7054	Approved
0.7882	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7472	Approved
0.784	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD3705	Approved
0.7815	Intermediate Similarity	NPD2796	Approved
0.7812	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2801	Approved
0.7806	Intermediate Similarity	NPD6799	Approved
0.7778	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7764	Intermediate Similarity	NPD5353	Approved
0.7758	Intermediate Similarity	NPD3926	Phase 2
0.7758	Intermediate Similarity	NPD5242	Approved
0.7746	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7199	Phase 2
0.7744	Intermediate Similarity	NPD1247	Approved
0.7714	Intermediate Similarity	NPD5536	Phase 2
0.7706	Intermediate Similarity	NPD7808	Phase 3
0.7702	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6232	Discontinued
0.7692	Intermediate Similarity	NPD6797	Phase 2
0.7676	Intermediate Similarity	NPD17	Approved
0.7673	Intermediate Similarity	NPD7458	Discontinued
0.7662	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD920	Approved
0.7651	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7251	Discontinued
0.7647	Intermediate Similarity	NPD6559	Discontinued
0.7632	Intermediate Similarity	NPD2799	Discontinued
0.7625	Intermediate Similarity	NPD6599	Discontinued
0.7605	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6166	Phase 2
0.7605	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7819	Suspended
0.7582	Intermediate Similarity	NPD2935	Discontinued
0.7574	Intermediate Similarity	NPD5844	Phase 1
0.7564	Intermediate Similarity	NPD3887	Approved
0.7561	Intermediate Similarity	NPD7075	Discontinued
0.7551	Intermediate Similarity	NPD2798	Approved
0.755	Intermediate Similarity	NPD447	Suspended
0.755	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6801	Discontinued
0.7517	Intermediate Similarity	NPD3972	Approved
0.7517	Intermediate Similarity	NPD1608	Approved
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7515	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4110	Phase 3
0.7468	Intermediate Similarity	NPD1511	Approved
0.7452	Intermediate Similarity	NPD6190	Approved
0.745	Intermediate Similarity	NPD6832	Phase 2
0.7444	Intermediate Similarity	NPD4420	Approved
0.7439	Intermediate Similarity	NPD5402	Approved
0.7436	Intermediate Similarity	NPD1243	Approved
0.7434	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5283	Phase 1
0.7421	Intermediate Similarity	NPD2532	Approved
0.7421	Intermediate Similarity	NPD2534	Approved
0.7421	Intermediate Similarity	NPD2533	Approved
0.7419	Intermediate Similarity	NPD7266	Discontinued
0.7415	Intermediate Similarity	NPD1876	Approved
0.7407	Intermediate Similarity	NPD7028	Phase 2
0.7405	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1510	Phase 2
0.7389	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1512	Approved
0.7372	Intermediate Similarity	NPD1549	Phase 2
0.7372	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2979	Phase 3
0.7368	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1240	Approved
0.7362	Intermediate Similarity	NPD7411	Suspended
0.7362	Intermediate Similarity	NPD6873	Phase 2
0.736	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7355	Intermediate Similarity	NPD2438	Suspended
0.7351	Intermediate Similarity	NPD2313	Discontinued
0.7351	Intermediate Similarity	NPD3764	Approved
0.7347	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3226	Approved
0.7341	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD5977	Approved
0.7333	Intermediate Similarity	NPD5978	Approved
0.733	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8127	Discontinued
0.732	Intermediate Similarity	NPD6355	Discontinued
0.7312	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3146	Approved
0.7312	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2346	Discontinued
0.7308	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2344	Approved
0.7308	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2353	Approved
0.7292	Intermediate Similarity	NPD9545	Approved
0.729	Intermediate Similarity	NPD3748	Approved
0.7283	Intermediate Similarity	NPD5006	Approved
0.7283	Intermediate Similarity	NPD5005	Approved
0.7273	Intermediate Similarity	NPD1465	Phase 2
0.7273	Intermediate Similarity	NPD1607	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5403	Approved
0.7211	Intermediate Similarity	NPD1281	Approved
0.7205	Intermediate Similarity	NPD5401	Approved
0.7197	Intermediate Similarity	NPD1471	Phase 3
0.7183	Intermediate Similarity	NPD1241	Discontinued
0.7179	Intermediate Similarity	NPD7033	Discontinued
0.7176	Intermediate Similarity	NPD6808	Phase 2
0.7171	Intermediate Similarity	NPD3027	Phase 3
0.7151	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7038	Approved
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD7039	Approved
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2354	Approved
0.7125	Intermediate Similarity	NPD2309	Approved
0.7124	Intermediate Similarity	NPD6798	Discontinued
0.7123	Intermediate Similarity	NPD1357	Approved
0.7123	Intermediate Similarity	NPD5585	Approved
0.7122	Intermediate Similarity	NPD1358	Approved
0.711	Intermediate Similarity	NPD3751	Discontinued
0.7099	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6233	Phase 2
0.7076	Intermediate Similarity	NPD3787	Discontinued
0.7073	Intermediate Similarity	NPD1653	Approved
0.7067	Intermediate Similarity	NPD1283	Approved
0.7066	Intermediate Similarity	NPD8455	Phase 2
0.7066	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3750	Approved
0.705	Intermediate Similarity	NPD3134	Approved
0.703	Intermediate Similarity	NPD3455	Phase 2
0.7025	Intermediate Similarity	NPD2531	Phase 2
0.7025	Intermediate Similarity	NPD1551	Phase 2
0.7022	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3266	Approved
0.702	Intermediate Similarity	NPD3267	Approved
0.7011	Intermediate Similarity	NPD2163	Approved
0.7007	Intermediate Similarity	NPD1651	Approved
0.7006	Intermediate Similarity	NPD6279	Approved
0.7006	Intermediate Similarity	NPD6280	Approved
0.7006	Intermediate Similarity	NPD7097	Phase 1
0.7	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7768	Phase 2
0.6982	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5647	Approved
0.6974	Remote Similarity	NPD1019	Discontinued
0.6972	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD8032	Phase 2
0.6968	Remote Similarity	NPD4062	Phase 3
0.6968	Remote Similarity	NPD7435	Discontinued
0.6964	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8166	Discontinued
0.6951	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3142	Approved
0.6923	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4307	Phase 2
0.6923	Remote Similarity	NPD3140	Approved
0.6919	Remote Similarity	NPD6959	Discontinued
0.6908	Remote Similarity	NPD1203	Approved
0.6903	Remote Similarity	NPD3268	Approved
0.6898	Remote Similarity	NPD6781	Approved
0.6898	Remote Similarity	NPD6782	Approved
0.6898	Remote Similarity	NPD6780	Approved
0.6898	Remote Similarity	NPD6777	Approved
0.6898	Remote Similarity	NPD6778	Approved
0.6898	Remote Similarity	NPD6779	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