NPASS Compound

Structure

NPC169645 OpenBabel07101718332D 49 53 0 0 1 0 0 0 0 0999 V2000 -3.5896 4.2306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4580 7.5763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 4.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 4.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9535 4.0050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2490 5.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0646 2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1445 4.5927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8670 4.4117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1625 5.9940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -0.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8417 4.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9715 5.4062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3776 -1.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2437 -1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9757 2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7691 4.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -0.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7078 4.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8851 5.8129 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5781 4.7738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 2.1970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6760 3.8239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2671 6.9885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8736 3.1915 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 -4.3776 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 3.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 40 1 0 0 0 0 2 41 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 19 1 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 9 16 2 0 0 0 0 10 44 1 0 0 0 0 11 31 1 0 0 0 0 11 45 1 0 0 0 0 12 31 1 0 0 0 0 12 46 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 20 2 0 0 0 0 15 40 1 0 0 0 0 16 20 1 0 0 0 0 16 41 1 0 0 0 0 17 25 2 0 0 0 0 17 42 1 0 0 0 0 18 10 1 6 0 0 0 18 21 1 0 0 0 0 18 47 1 0 0 0 0 19 32 2 0 0 0 0 19 48 1 0 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 21 34 1 1 0 0 0 22 23 1 0 0 0 0 22 35 1 6 0 0 0 23 29 1 0 0 0 0 23 36 1 1 0 0 0 24 26 2 0 0 0 0 24 48 1 0 0 0 0 25 26 1 0 0 0 0 25 49 1 0 0 0 0 26 43 1 0 0 0 0 27 30 1 0 0 0 0 27 31 1 6 0 0 0 27 37 1 0 0 0 0 28 38 2 0 0 0 0 28 45 1 0 0 0 0 29 47 1 0 0 0 0 29 49 1 6 0 0 0 30 44 1 1 0 0 0 30 46 1 0 0 0 0 31 39 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	696.19
Volume:	636.446
LogP:	0.825
LogD:	0.352
LogS:	-3.075
# Rotatable Bonds:	13
TPSA:	251.73
# H-Bond Aceptor:	18
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.099
Synthetic Accessibility Score:	4.858
Fsp3:	0.484
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.348
MDCK Permeability:	4.263754817657173e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.725
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.345
Plasma Protein Binding (PPB):	54.094871520996094%
Volume Distribution (VD):	0.593
Pgp-substrate:	33.08515930175781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.984
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.133
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.143
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	3.366
Half-life (T1/2):	0.862

ADMET: Toxicity

hERG Blockers:	0.62
Human Hepatotoxicity (H-HT):	0.508
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.201
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.12
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC169645

Natural Product ID:	NPC169645
*Common Name:**	Eryciboside F
IUPAC Name:	[(3S,4R,5R)-5-[[(2R,3S,4S,5R,6S)-6-(6,8-dimethoxy-2-oxochromen-7-yl)oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxy-3,5-dimethoxybenzoate
Synonyms:	eryciboside F
Standard InCHIKey:	YIKMDUILDWUKKL-LJCQSLGBSA-N
Standard InCHI:	InChI=1S/C31H36O18/c1-40-15-8-14(9-16(41-2)20(15)33)28(38)45-11-31(39)12-46-30(27(31)37)44-10-18-21(34)22(35)23(36)29(47-18)49-25-17(42-3)7-13-5-6-19(32)48-24(13)26(25)43-4/h5-9,18,21-23,27,29-30,33-37,39H,10-12H2,1-4H3/t18-,21-,22+,23-,27+,29+,30-,31-/m1/s1
SMILES:	COc1cc2ccc(=O)oc2c(c1O[C@@H]1O[C@H](CO[C@@H]2OC[C@]([C@H]2O)(O)COC(=O)c2cc(OC)c(c(c2)OC)O)[C@H]([C@@H]([C@H]1O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076769
PubChem CID:	46185077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO32755	erycibe hainanesis	Species	Convolvulaceae	Eukaryota	roots and stems	Hainan Province, China	2008-Mar	PMID[20092289]

☑ 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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Survival	=	44.0	%	PMID[490696]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	15.5	%	PMID[490696]

☑ 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 NPC169645 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	430
0.1-0.2	1807
0.2-0.3	4095
0.3-0.4	9226
0.4-0.5	9305
0.5-0.6	4885
0.6-0.7	5873
0.7-0.8	5322
0.8-0.85	1083
0.85-0.9	554
0.9-0.95	113
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC84482
0.9695	High Similarity	NPC163165
0.9383	High Similarity	NPC311803
0.9383	High Similarity	NPC472859
0.9383	High Similarity	NPC25389
0.9345	High Similarity	NPC257714
0.9321	High Similarity	NPC119125
0.9321	High Similarity	NPC166277
0.9281	High Similarity	NPC102851
0.9281	High Similarity	NPC254540
0.9281	High Similarity	NPC172807
0.9281	High Similarity	NPC211594
0.9281	High Similarity	NPC5786
0.9259	High Similarity	NPC289811
0.9259	High Similarity	NPC160780
0.9259	High Similarity	NPC287872
0.9259	High Similarity	NPC74319
0.924	High Similarity	NPC199172
0.924	High Similarity	NPC35924
0.9207	High Similarity	NPC90905
0.9207	High Similarity	NPC33298
0.9207	High Similarity	NPC285108
0.9207	High Similarity	NPC4013
0.9202	High Similarity	NPC239966
0.9202	High Similarity	NPC203020
0.9198	High Similarity	NPC1913
0.9172	High Similarity	NPC477848
0.9167	High Similarity	NPC307518
0.9167	High Similarity	NPC48773
0.9167	High Similarity	NPC235575
0.9167	High Similarity	NPC205076
0.9162	High Similarity	NPC93337
0.9162	High Similarity	NPC658
0.9162	High Similarity	NPC226294
0.9162	High Similarity	NPC58053
0.9162	High Similarity	NPC469931
0.9162	High Similarity	NPC197708
0.9162	High Similarity	NPC45638
0.9162	High Similarity	NPC475942
0.9162	High Similarity	NPC186807
0.9162	High Similarity	NPC105025
0.9162	High Similarity	NPC201292
0.9128	High Similarity	NPC470447
0.9128	High Similarity	NPC470446
0.9128	High Similarity	NPC470445
0.9128	High Similarity	NPC470449
0.9128	High Similarity	NPC473072
0.9118	High Similarity	NPC473713
0.9118	High Similarity	NPC198324
0.9118	High Similarity	NPC211532
0.9118	High Similarity	NPC472385
0.9118	High Similarity	NPC233994
0.9118	High Similarity	NPC472991
0.9118	High Similarity	NPC472992
0.9112	High Similarity	NPC204693
0.9107	High Similarity	NPC105511
0.9107	High Similarity	NPC224462
0.9107	High Similarity	NPC212748
0.9102	High Similarity	NPC116745
0.9102	High Similarity	NPC146792
0.9102	High Similarity	NPC45618
0.9102	High Similarity	NPC58716
0.9096	High Similarity	NPC142614
0.9085	High Similarity	NPC289346
0.908	High Similarity	NPC226759
0.908	High Similarity	NPC472860
0.9075	High Similarity	NPC470455
0.9075	High Similarity	NPC470451
0.907	High Similarity	NPC473071
0.907	High Similarity	NPC473073
0.9059	High Similarity	NPC43211
0.9059	High Similarity	NPC135277
0.9059	High Similarity	NPC469354
0.9059	High Similarity	NPC101191
0.9059	High Similarity	NPC472607
0.9059	High Similarity	NPC210094
0.9059	High Similarity	NPC237435
0.9059	High Similarity	NPC115760
0.9059	High Similarity	NPC49344
0.9059	High Similarity	NPC264735
0.9053	High Similarity	NPC472386
0.9053	High Similarity	NPC117260
0.9053	High Similarity	NPC259152
0.9053	High Similarity	NPC476405
0.9053	High Similarity	NPC3583
0.9053	High Similarity	NPC261254
0.9048	High Similarity	NPC198125
0.9048	High Similarity	NPC95421
0.903	High Similarity	NPC217950
0.9017	High Similarity	NPC36138
0.9012	High Similarity	NPC327032
0.9012	High Similarity	NPC191046
0.9012	High Similarity	NPC194095
0.9012	High Similarity	NPC470443
0.9012	High Similarity	NPC473682
0.9012	High Similarity	NPC473571
0.9012	High Similarity	NPC110941
0.9012	High Similarity	NPC241423
0.9012	High Similarity	NPC470444
0.9012	High Similarity	NPC126784
0.9006	High Similarity	NPC169733
0.9006	High Similarity	NPC67629
0.9006	High Similarity	NPC79736
0.9	High Similarity	NPC175230
0.9	High Similarity	NPC101026
0.9	High Similarity	NPC172033
0.9	High Similarity	NPC4390
0.9	High Similarity	NPC42773
0.9	High Similarity	NPC88560
0.9	High Similarity	NPC24043
0.9	High Similarity	NPC472993
0.9	High Similarity	NPC45522
0.9	High Similarity	NPC169977
0.9	High Similarity	NPC21666
0.8994	High Similarity	NPC245014
0.8994	High Similarity	NPC84265
0.8994	High Similarity	NPC282987
0.8994	High Similarity	NPC183357
0.8994	High Similarity	NPC21190
0.8994	High Similarity	NPC34287
0.8994	High Similarity	NPC471416
0.8994	High Similarity	NPC22195
0.8994	High Similarity	NPC204937
0.8994	High Similarity	NPC474434
0.8994	High Similarity	NPC149011
0.8994	High Similarity	NPC44558
0.8988	High Similarity	NPC135345
0.8988	High Similarity	NPC229729
0.8982	High Similarity	NPC22832
0.8982	High Similarity	NPC311830
0.8976	High Similarity	NPC148273
0.8966	High Similarity	NPC470416
0.8963	High Similarity	NPC133984
0.896	High Similarity	NPC469371
0.8953	High Similarity	NPC241196
0.8953	High Similarity	NPC120952
0.8953	High Similarity	NPC476620
0.8953	High Similarity	NPC476618
0.8953	High Similarity	NPC173837
0.8953	High Similarity	NPC472387
0.8953	High Similarity	NPC476619
0.8953	High Similarity	NPC476773
0.8953	High Similarity	NPC476622
0.8953	High Similarity	NPC476623
0.8953	High Similarity	NPC476621
0.8953	High Similarity	NPC267549
0.8951	High Similarity	NPC310661
0.8951	High Similarity	NPC105827
0.8947	High Similarity	NPC142996
0.8947	High Similarity	NPC102028
0.8941	High Similarity	NPC245452
0.8941	High Similarity	NPC190003
0.8941	High Similarity	NPC175107
0.8941	High Similarity	NPC153755
0.8941	High Similarity	NPC475155
0.8935	High Similarity	NPC209296
0.8935	High Similarity	NPC210042
0.8935	High Similarity	NPC86008
0.8935	High Similarity	NPC472383
0.8935	High Similarity	NPC472381
0.8935	High Similarity	NPC195257
0.8935	High Similarity	NPC170675
0.8935	High Similarity	NPC183036
0.8935	High Similarity	NPC112755
0.8935	High Similarity	NPC149300
0.8935	High Similarity	NPC95855
0.8935	High Similarity	NPC229687
0.8935	High Similarity	NPC471457
0.8929	High Similarity	NPC99957
0.8929	High Similarity	NPC181616
0.8922	High Similarity	NPC309025
0.8922	High Similarity	NPC191306
0.8922	High Similarity	NPC94777
0.8922	High Similarity	NPC19709
0.8922	High Similarity	NPC222936
0.8922	High Similarity	NPC88043
0.8922	High Similarity	NPC88023
0.8922	High Similarity	NPC168822
0.8922	High Similarity	NPC284960
0.8922	High Similarity	NPC243930
0.8922	High Similarity	NPC270335
0.8908	High Similarity	NPC107987
0.8902	High Similarity	NPC471405
0.8902	High Similarity	NPC471030
0.8895	High Similarity	NPC296018
0.8895	High Similarity	NPC65563
0.8895	High Similarity	NPC472382
0.8895	High Similarity	NPC268533
0.8895	High Similarity	NPC154741
0.8895	High Similarity	NPC8573
0.8895	High Similarity	NPC89127
0.8895	High Similarity	NPC470949
0.8895	High Similarity	NPC471669
0.8895	High Similarity	NPC472380
0.8895	High Similarity	NPC297574
0.8895	High Similarity	NPC472384
0.8889	High Similarity	NPC36130
0.8889	High Similarity	NPC34436
0.8889	High Similarity	NPC219600
0.8889	High Similarity	NPC51774

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 NPC169645 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	919
0.2-0.3	2132
0.3-0.4	2739
0.4-0.5	1858
0.5-0.6	775
0.6-0.7	237
0.7-0.8	102
0.8-0.85	13
0.85-0.9	7
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9059	High Similarity	NPD4338	Clinical (unspecified phase)
0.8994	High Similarity	NPD7472	Approved
0.8988	High Similarity	NPD3818	Discontinued
0.8935	High Similarity	NPD7054	Approved
0.8779	High Similarity	NPD7251	Discontinued
0.8772	High Similarity	NPD7074	Phase 3
0.8728	High Similarity	NPD7808	Phase 3
0.8721	High Similarity	NPD6797	Phase 2
0.8704	High Similarity	NPD1653	Approved
0.8675	High Similarity	NPD4868	Clinical (unspecified phase)
0.8563	High Similarity	NPD7685	Pre-registration
0.8512	High Similarity	NPD4381	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD2801	Approved
0.8391	Intermediate Similarity	NPD5844	Phase 1
0.8295	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD1934	Approved
0.8235	Intermediate Similarity	NPD3882	Suspended
0.8229	Intermediate Similarity	NPD7228	Approved
0.8225	Intermediate Similarity	NPD1465	Phase 2
0.8218	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD6166	Phase 2
0.8218	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8167	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD6559	Discontinued
0.8118	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD5494	Approved
0.8084	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD5402	Approved
0.8046	Intermediate Similarity	NPD7199	Phase 2
0.8035	Intermediate Similarity	NPD6234	Discontinued
0.7977	Intermediate Similarity	NPD7075	Discontinued
0.7953	Intermediate Similarity	NPD37	Approved
0.7946	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD4380	Phase 2
0.7919	Intermediate Similarity	NPD4966	Approved
0.7919	Intermediate Similarity	NPD4965	Approved
0.7919	Intermediate Similarity	NPD4967	Phase 2
0.7904	Intermediate Similarity	NPD1511	Approved
0.7892	Intermediate Similarity	NPD6190	Approved
0.7866	Intermediate Similarity	NPD7266	Discontinued
0.7853	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD7240	Approved
0.7838	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD1512	Approved
0.7803	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7746	Intermediate Similarity	NPD6801	Discontinued
0.7701	Intermediate Similarity	NPD7819	Suspended
0.7697	Intermediate Similarity	NPD6232	Discontinued
0.7667	Intermediate Similarity	NPD7473	Discontinued
0.7663	Intermediate Similarity	NPD8312	Approved
0.7663	Intermediate Similarity	NPD8313	Approved
0.7661	Intermediate Similarity	NPD5403	Approved
0.7624	Intermediate Similarity	NPD3751	Discontinued
0.76	Intermediate Similarity	NPD8455	Phase 2
0.7588	Intermediate Similarity	NPD6799	Approved
0.7586	Intermediate Similarity	NPD7411	Suspended
0.7571	Intermediate Similarity	NPD3749	Approved
0.7563	Intermediate Similarity	NPD7585	Approved
0.7544	Intermediate Similarity	NPD5401	Approved
0.7538	Intermediate Similarity	NPD7435	Discontinued
0.7538	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7783	Phase 2
0.7528	Intermediate Similarity	NPD919	Approved
0.7515	Intermediate Similarity	NPD3750	Approved
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.7513	Intermediate Similarity	NPD7583	Approved
0.75	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7485	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD447	Suspended
0.7455	Intermediate Similarity	NPD1933	Approved
0.7447	Intermediate Similarity	NPD8434	Phase 2
0.7444	Intermediate Similarity	NPD1247	Approved
0.7442	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD8151	Discontinued
0.7423	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD6776	Approved
0.7385	Intermediate Similarity	NPD6781	Approved
0.7385	Intermediate Similarity	NPD6778	Approved
0.7385	Intermediate Similarity	NPD6779	Approved
0.7385	Intermediate Similarity	NPD6780	Approved
0.7385	Intermediate Similarity	NPD6777	Approved
0.7385	Intermediate Similarity	NPD6782	Approved
0.7381	Intermediate Similarity	NPD2796	Approved
0.736	Intermediate Similarity	NPD5353	Approved
0.736	Intermediate Similarity	NPD7680	Approved
0.7337	Intermediate Similarity	NPD7584	Approved
0.733	Intermediate Similarity	NPD6599	Discontinued
0.7322	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1510	Phase 2
0.7318	Intermediate Similarity	NPD7768	Phase 2
0.7317	Intermediate Similarity	NPD3027	Phase 3
0.7313	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7874	Approved
0.7294	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2935	Discontinued
0.7278	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD7697	Approved
0.7273	Intermediate Similarity	NPD7696	Phase 3
0.7273	Intermediate Similarity	NPD7698	Approved
0.7268	Intermediate Similarity	NPD3926	Phase 2
0.7257	Intermediate Similarity	NPD920	Approved
0.7256	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6959	Discontinued
0.7253	Intermediate Similarity	NPD8127	Discontinued
0.7251	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2532	Approved
0.7241	Intermediate Similarity	NPD2533	Approved
0.7241	Intermediate Similarity	NPD2534	Approved
0.7241	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7871	Phase 2
0.7236	Intermediate Similarity	NPD7870	Phase 2
0.7234	Intermediate Similarity	NPD7549	Discontinued
0.7222	Intermediate Similarity	NPD6823	Phase 2
0.7219	Intermediate Similarity	NPD3748	Approved
0.7214	Intermediate Similarity	NPD7701	Phase 2
0.7209	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD9494	Approved
0.7195	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7458	Discontinued
0.7158	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6535	Approved
0.7128	Intermediate Similarity	NPD6534	Approved
0.7118	Intermediate Similarity	NPD7033	Discontinued
0.7108	Intermediate Similarity	NPD7801	Approved
0.7107	Intermediate Similarity	NPD7700	Phase 2
0.7107	Intermediate Similarity	NPD7699	Phase 2
0.7099	Intermediate Similarity	NPD9269	Phase 2
0.7095	Intermediate Similarity	NPD6385	Approved
0.7095	Intermediate Similarity	NPD6386	Approved
0.7083	Intermediate Similarity	NPD943	Approved
0.7083	Intermediate Similarity	NPD1240	Approved
0.7083	Intermediate Similarity	NPD8150	Discontinued
0.7081	Intermediate Similarity	NPD5242	Approved
0.7056	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD1243	Approved
0.7052	Intermediate Similarity	NPD6674	Discontinued
0.7048	Intermediate Similarity	NPD6832	Phase 2
0.7037	Intermediate Similarity	NPD1091	Approved
0.7029	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7229	Phase 3
0.7024	Intermediate Similarity	NPD6233	Phase 2
0.7018	Intermediate Similarity	NPD4308	Phase 3
0.7012	Intermediate Similarity	NPD3225	Approved
0.7	Intermediate Similarity	NPD1607	Approved
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7038	Approved
0.7	Intermediate Similarity	NPD7039	Approved
0.6983	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3226	Approved
0.698	Remote Similarity	NPD8320	Phase 1
0.698	Remote Similarity	NPD8319	Approved
0.6977	Remote Similarity	NPD6099	Approved
0.6977	Remote Similarity	NPD6100	Approved
0.697	Remote Similarity	NPD1203	Approved
0.6967	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6844	Discontinued
0.6959	Remote Similarity	NPD7097	Phase 1
0.6951	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5953	Discontinued
0.6941	Remote Similarity	NPD6355	Discontinued
0.6941	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD422	Phase 1
0.6931	Remote Similarity	NPD7286	Phase 2
0.6923	Remote Similarity	NPD7930	Approved
0.691	Remote Similarity	NPD6273	Approved
0.6901	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5006	Approved
0.6881	Remote Similarity	NPD5005	Approved
0.6867	Remote Similarity	NPD2797	Approved
0.6864	Remote Similarity	NPD6798	Discontinued
0.6864	Remote Similarity	NPD3268	Approved
0.6864	Remote Similarity	NPD3764	Approved
0.6857	Remote Similarity	NPD2800	Approved
0.6852	Remote Similarity	NPD9268	Approved
0.6845	Remote Similarity	NPD5710	Approved
0.6845	Remote Similarity	NPD5711	Approved
0.6845	Remote Similarity	NPD4908	Phase 1
0.6818	Remote Similarity	NPD6213	Phase 3
0.6818	Remote Similarity	NPD6212	Phase 3
0.6818	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4357	Discontinued
0.6793	Remote Similarity	NPD4288	Approved
0.679	Remote Similarity	NPD9545	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