NPASS Compound

Structure

NPC206823 OpenBabel07101718322D 49 52 0 0 1 0 0 0 0 0999 V2000 -0.3636 3.1266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 3.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2446 -5.1802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3192 3.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0522 2.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0891 -2.3898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0891 -1.3898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7944 -3.3454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7944 -0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2310 -4.1716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0078 3.0359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2310 0.3920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4492 -4.7951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7409 2.3558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4492 1.0155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5183 -5.1604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9284 -0.0193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 2.7331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2697 -4.9577 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5183 1.3808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1466 -0.6428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5211 -5.2352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5895 -5.6907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1859 2.2331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2956 -1.6317 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3854 -5.4682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1859 1.2331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5138 -2.2551 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6802 -4.5127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6802 0.7331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5829 -1.8898 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5462 1.2331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -3.7796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4339 -0.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8593 -0.3847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4464 -6.2324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8843 -6.6463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0519 2.7331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2265 -1.9970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0656 -6.2013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0519 0.7331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -3.2440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5462 2.2331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -4.0021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5211 1.4556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2157 -0.2775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5462 -5.0127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 -2.8786 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 4 1 0 0 0 0 4 5 1 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 17 35 1 0 0 0 0 18 2 1 6 0 0 0 18 24 1 0 0 0 0 18 43 1 0 0 0 0 19 3 1 6 0 0 0 19 23 1 0 0 0 0 19 44 1 0 0 0 0 20 14 1 6 0 0 0 20 45 1 0 0 0 0 21 17 1 6 0 0 0 21 25 1 0 0 0 0 21 46 1 0 0 0 0 22 36 2 0 0 0 0 22 47 1 0 0 0 0 23 26 1 0 0 0 0 23 37 1 1 0 0 0 24 27 1 0 0 0 0 24 38 1 6 0 0 0 25 28 1 0 0 0 0 25 39 1 1 0 0 0 26 29 1 0 0 0 0 26 40 1 6 0 0 0 27 30 1 0 0 0 0 27 41 1 6 0 0 0 28 31 1 0 0 0 0 28 42 1 6 0 0 0 29 33 1 0 0 0 0 29 47 1 1 0 0 0 30 32 1 0 0 0 0 30 49 1 1 0 0 0 31 34 1 0 0 0 0 31 48 1 1 0 0 0 32 43 1 6 0 0 0 32 45 1 0 0 0 0 33 44 1 6 0 0 0 33 48 1 0 0 0 0 34 46 1 6 0 0 0 34 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	708.39
Volume:	691.611
LogP:	3.48
LogD:	3.217
LogS:	-3.912
# Rotatable Bonds:	5
TPSA:	223.29
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.153
Synthetic Accessibility Score:	5.821
Fsp3:	0.971
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.828
MDCK Permeability:	6.780856347177178e-05
Pgp-inhibitor:	0.571
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.95
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	90.73302459716797%
Volume Distribution (VD):	0.542
Pgp-substrate:	6.532181262969971%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	1.058
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.496
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.133
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.889
Carcinogencity:	0.123
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.143

Download Data

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

Natural Product: NPC206823

Natural Product ID:	NPC206823
*Common Name:**	Tricolorin F
IUPAC Name:	n.a.
Synonyms:	Tricolorin F
Standard InCHIKey:	BLGCNDRGZMCMJB-DMPWARCPSA-N
Standard InCHI:	InChI=1S/C34H60O15/c1-4-5-11-14-20-15-12-9-7-6-8-10-13-16-22(36)47-29-26(40)23(37)19(3)44-33(29)48-31-28(42)25(39)21(17-35)46-34(31)49-30-27(41)24(38)18(2)43-32(30)45-20/h18-21,23-35,37-42H,4-17H2,1-3H3/t18-,19-,20+,21-,23-,24+,25-,26+,27+,28+,29-,30-,31-,32+,33+,34+/m1/s1
SMILES:	CCCCC[C@H]1CCCCCCCCCC(=O)O[C@H]2[C@H](O[C@H]3[C@H](O[C@H]4[C@H](O1)O[C@H](C)[C@@H]([C@@H]4O)O)O[C@H](CO)[C@H]([C@@H]3O)O)O[C@H](C)[C@H]([C@@H]2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446864
PubChem CID:	11331512
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	DOI[10.1016/S0040-4020(97)00607-8]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	PMID[16562846]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8496705]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	512.0	ug.mL-1	PMID[525184]

☑ 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 NPC206823 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	703
0.1-0.2	4499
0.2-0.3	13528
0.3-0.4	11496
0.4-0.5	7187
0.5-0.6	4144
0.6-0.7	955
0.7-0.8	70
0.8-0.85	24
0.85-0.9	73
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC9763
0.9706	High Similarity	NPC39266
0.9706	High Similarity	NPC169085
0.9706	High Similarity	NPC225748
0.9706	High Similarity	NPC163812
0.9571	High Similarity	NPC477350
0.9552	High Similarity	NPC285003
0.9552	High Similarity	NPC211428
0.9552	High Similarity	NPC241265
0.9437	High Similarity	NPC476782
0.9437	High Similarity	NPC216883
0.9437	High Similarity	NPC476781
0.9437	High Similarity	NPC476783
0.9403	High Similarity	NPC97736
0.9403	High Similarity	NPC50228
0.9306	High Similarity	NPC477323
0.9306	High Similarity	NPC475425
0.9306	High Similarity	NPC477328
0.9306	High Similarity	NPC281563
0.9306	High Similarity	NPC477329
0.9306	High Similarity	NPC477320
0.9306	High Similarity	NPC146380
0.9306	High Similarity	NPC113745
0.9306	High Similarity	NPC109887
0.9306	High Similarity	NPC477330
0.9306	High Similarity	NPC477326
0.9306	High Similarity	NPC477325
0.9254	High Similarity	NPC206601
0.9178	High Similarity	NPC146992
0.9178	High Similarity	NPC477344
0.9178	High Similarity	NPC477346
0.9178	High Similarity	NPC158302
0.9178	High Similarity	NPC85759
0.9178	High Similarity	NPC294748
0.9178	High Similarity	NPC22742
0.9118	High Similarity	NPC67099
0.9118	High Similarity	NPC250619
0.9054	High Similarity	NPC267592
0.8955	High Similarity	NPC76881
0.8955	High Similarity	NPC190418
0.8955	High Similarity	NPC12040
0.8955	High Similarity	NPC471761
0.8955	High Similarity	NPC471760
0.8933	High Similarity	NPC123204
0.8933	High Similarity	NPC477319
0.8933	High Similarity	NPC475270
0.8933	High Similarity	NPC477331
0.8933	High Similarity	NPC89843
0.8933	High Similarity	NPC143421
0.8933	High Similarity	NPC269318
0.8933	High Similarity	NPC307400
0.8933	High Similarity	NPC475667
0.8933	High Similarity	NPC472204
0.8933	High Similarity	NPC224953
0.8933	High Similarity	NPC27289
0.8933	High Similarity	NPC472201
0.8933	High Similarity	NPC183888
0.8933	High Similarity	NPC238056
0.8933	High Similarity	NPC44782
0.8933	High Similarity	NPC477318
0.8933	High Similarity	NPC119583
0.8933	High Similarity	NPC472205
0.8933	High Similarity	NPC186992
0.8933	High Similarity	NPC477347
0.8933	High Similarity	NPC184915
0.8933	High Similarity	NPC297768
0.8933	High Similarity	NPC169345
0.8933	High Similarity	NPC477317
0.8933	High Similarity	NPC115013
0.8933	High Similarity	NPC259294
0.8933	High Similarity	NPC173328
0.8933	High Similarity	NPC126685
0.8933	High Similarity	NPC472202
0.8933	High Similarity	NPC475327
0.8933	High Similarity	NPC476087
0.8933	High Similarity	NPC290012
0.8933	High Similarity	NPC472203
0.8933	High Similarity	NPC472200
0.8873	High Similarity	NPC308096
0.8873	High Similarity	NPC291228
0.8857	High Similarity	NPC52268
0.8857	High Similarity	NPC53760
0.8732	High Similarity	NPC185419
0.8732	High Similarity	NPC184550
0.8701	High Similarity	NPC477332
0.8701	High Similarity	NPC60849
0.8701	High Similarity	NPC472352
0.8657	High Similarity	NPC325773
0.8358	Intermediate Similarity	NPC477753
0.8358	Intermediate Similarity	NPC477750
0.8358	Intermediate Similarity	NPC477757
0.8358	Intermediate Similarity	NPC477762
0.8358	Intermediate Similarity	NPC477763
0.8358	Intermediate Similarity	NPC477755
0.8228	Intermediate Similarity	NPC473500
0.8228	Intermediate Similarity	NPC38295
0.8228	Intermediate Similarity	NPC156089
0.8228	Intermediate Similarity	NPC470313
0.7975	Intermediate Similarity	NPC21693
0.7975	Intermediate Similarity	NPC236649
0.791	Intermediate Similarity	NPC472025
0.7882	Intermediate Similarity	NPC477349
0.7831	Intermediate Similarity	NPC51662
0.7794	Intermediate Similarity	NPC317023
0.7778	Intermediate Similarity	NPC477751
0.7778	Intermediate Similarity	NPC477752
0.7778	Intermediate Similarity	NPC477764
0.7778	Intermediate Similarity	NPC477756
0.7761	Intermediate Similarity	NPC148424
0.7701	Intermediate Similarity	NPC477348
0.7701	Intermediate Similarity	NPC163409
0.7701	Intermediate Similarity	NPC238264
0.7701	Intermediate Similarity	NPC477345
0.7701	Intermediate Similarity	NPC44682
0.7671	Intermediate Similarity	NPC477761
0.7671	Intermediate Similarity	NPC477759
0.7671	Intermediate Similarity	NPC477758
0.7671	Intermediate Similarity	NPC477760
0.7671	Intermediate Similarity	NPC477754
0.7654	Intermediate Similarity	NPC248415
0.759	Intermediate Similarity	NPC83839
0.7536	Intermediate Similarity	NPC322855
0.7536	Intermediate Similarity	NPC320032
0.7528	Intermediate Similarity	NPC475241
0.7528	Intermediate Similarity	NPC475540
0.7528	Intermediate Similarity	NPC475525
0.7528	Intermediate Similarity	NPC473765
0.7528	Intermediate Similarity	NPC473605
0.7528	Intermediate Similarity	NPC475375
0.7528	Intermediate Similarity	NPC475164
0.7528	Intermediate Similarity	NPC476066
0.7528	Intermediate Similarity	NPC475593
0.75	Intermediate Similarity	NPC6848
0.75	Intermediate Similarity	NPC470657
0.747	Intermediate Similarity	NPC288471
0.7468	Intermediate Similarity	NPC110813
0.7463	Intermediate Similarity	NPC469937
0.7463	Intermediate Similarity	NPC320588
0.7463	Intermediate Similarity	NPC303727
0.7463	Intermediate Similarity	NPC23155
0.7463	Intermediate Similarity	NPC53463
0.7432	Intermediate Similarity	NPC32148
0.7412	Intermediate Similarity	NPC314364
0.7412	Intermediate Similarity	NPC31349
0.7375	Intermediate Similarity	NPC133377
0.7361	Intermediate Similarity	NPC268243
0.7313	Intermediate Similarity	NPC107914
0.7313	Intermediate Similarity	NPC67660
0.7313	Intermediate Similarity	NPC165198
0.7313	Intermediate Similarity	NPC242073
0.7313	Intermediate Similarity	NPC246558
0.7313	Intermediate Similarity	NPC157514
0.7313	Intermediate Similarity	NPC89145
0.7313	Intermediate Similarity	NPC58629
0.7313	Intermediate Similarity	NPC269166
0.7313	Intermediate Similarity	NPC145112
0.7286	Intermediate Similarity	NPC34877
0.7286	Intermediate Similarity	NPC290179
0.7262	Intermediate Similarity	NPC125253
0.7262	Intermediate Similarity	NPC253975
0.7262	Intermediate Similarity	NPC192025
0.725	Intermediate Similarity	NPC474003
0.7143	Intermediate Similarity	NPC321873
0.7143	Intermediate Similarity	NPC143446
0.7126	Intermediate Similarity	NPC470009
0.7083	Intermediate Similarity	NPC472026
0.7033	Intermediate Similarity	NPC215570
0.7021	Intermediate Similarity	NPC188453
0.7021	Intermediate Similarity	NPC42320
0.7015	Intermediate Similarity	NPC23134
0.7015	Intermediate Similarity	NPC124963
0.7015	Intermediate Similarity	NPC326533
0.7015	Intermediate Similarity	NPC233726
0.7	Intermediate Similarity	NPC320089
0.6979	Remote Similarity	NPC469827
0.6962	Remote Similarity	NPC55652
0.6944	Remote Similarity	NPC470363
0.6889	Remote Similarity	NPC472197
0.6882	Remote Similarity	NPC472273
0.6866	Remote Similarity	NPC55678
0.686	Remote Similarity	NPC473791
0.6842	Remote Similarity	NPC476611
0.6837	Remote Similarity	NPC126753
0.6837	Remote Similarity	NPC287269
0.6829	Remote Similarity	NPC244002
0.6812	Remote Similarity	NPC323361
0.6812	Remote Similarity	NPC130683
0.6786	Remote Similarity	NPC163362
0.6786	Remote Similarity	NPC127295
0.6771	Remote Similarity	NPC310031
0.6771	Remote Similarity	NPC80191
0.6771	Remote Similarity	NPC94919
0.6771	Remote Similarity	NPC227622
0.6768	Remote Similarity	NPC469826
0.6768	Remote Similarity	NPC207693
0.6753	Remote Similarity	NPC286842
0.6744	Remote Similarity	NPC474266
0.6737	Remote Similarity	NPC20028
0.6716	Remote Similarity	NPC299781
0.6716	Remote Similarity	NPC26253

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 NPC206823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	779
0.1-0.2	4183
0.2-0.3	2821
0.3-0.4	813
0.4-0.5	331
0.5-0.6	158
0.6-0.7	53
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7949	Intermediate Similarity	NPD7329	Approved
0.7571	Intermediate Similarity	NPD6123	Approved
0.7463	Intermediate Similarity	NPD3728	Approved
0.7463	Intermediate Similarity	NPD3730	Approved
0.7432	Intermediate Similarity	NPD897	Approved
0.7432	Intermediate Similarity	NPD898	Approved
0.7432	Intermediate Similarity	NPD896	Approved
0.7403	Intermediate Similarity	NPD3181	Approved
0.7313	Intermediate Similarity	NPD892	Phase 3
0.7313	Intermediate Similarity	NPD888	Phase 3
0.7313	Intermediate Similarity	NPD891	Phase 3
0.7313	Intermediate Similarity	NPD893	Approved
0.7313	Intermediate Similarity	NPD890	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7346	Approved
0.7164	Intermediate Similarity	NPD2269	Approved
0.7015	Intermediate Similarity	NPD904	Phase 3
0.7015	Intermediate Similarity	NPD905	Approved
0.6812	Remote Similarity	NPD894	Approved
0.6812	Remote Similarity	NPD889	Approved
0.6812	Remote Similarity	NPD895	Approved
0.6812	Remote Similarity	NPD887	Approved
0.6771	Remote Similarity	NPD8082	Approved
0.6771	Remote Similarity	NPD8086	Approved
0.6771	Remote Similarity	NPD8085	Approved
0.6771	Remote Similarity	NPD8084	Approved
0.6771	Remote Similarity	NPD8083	Approved
0.6771	Remote Similarity	NPD8138	Approved
0.6771	Remote Similarity	NPD8139	Approved
0.6761	Remote Similarity	NPD2267	Suspended
0.6701	Remote Similarity	NPD8275	Approved
0.6701	Remote Similarity	NPD8276	Approved
0.6667	Remote Similarity	NPD8961	Approved
0.6633	Remote Similarity	NPD8081	Approved
0.6633	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8393	Approved
0.6552	Remote Similarity	NPD3669	Approved
0.6552	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8140	Approved
0.65	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8307	Discontinued
0.6442	Remote Similarity	NPD8133	Approved
0.6373	Remote Similarity	NPD8305	Approved
0.6373	Remote Similarity	NPD8306	Approved
0.6373	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7909	Approved
0.6322	Remote Similarity	NPD1780	Approved
0.6322	Remote Similarity	NPD1779	Approved
0.6311	Remote Similarity	NPD8087	Discontinued
0.6275	Remote Similarity	NPD6686	Approved
0.6269	Remote Similarity	NPD9000	Phase 3
0.6269	Remote Similarity	NPD8998	Phase 2
0.6269	Remote Similarity	NPD8993	Phase 1
0.6269	Remote Similarity	NPD8997	Approved
0.6269	Remote Similarity	NPD8999	Phase 3
0.6263	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7140	Approved
0.6263	Remote Similarity	NPD7139	Approved
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8959	Approved
0.6216	Remote Similarity	NPD369	Approved
0.6214	Remote Similarity	NPD6941	Approved
0.6119	Remote Similarity	NPD2699	Approved
0.6111	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1447	Phase 3
0.6105	Remote Similarity	NPD8171	Discontinued
0.6105	Remote Similarity	NPD1446	Phase 3
0.6091	Remote Similarity	NPD8346	Approved
0.6091	Remote Similarity	NPD8347	Approved
0.6091	Remote Similarity	NPD8345	Approved
0.6087	Remote Similarity	NPD8965	Approved
0.6087	Remote Similarity	NPD8966	Approved
0.6082	Remote Similarity	NPD6428	Approved
0.6081	Remote Similarity	NPD73	Approved
0.6064	Remote Similarity	NPD6698	Approved
0.6064	Remote Similarity	NPD46	Approved
0.6036	Remote Similarity	NPD8516	Approved
0.6036	Remote Similarity	NPD8517	Approved
0.6036	Remote Similarity	NPD8515	Approved
0.6036	Remote Similarity	NPD8513	Phase 3
0.6027	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD847	Phase 1
0.6022	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.596	Remote Similarity	NPD2255	Approved
0.5941	Remote Similarity	NPD8301	Approved
0.5941	Remote Similarity	NPD8300	Approved
0.589	Remote Similarity	NPD9036	Phase 3
0.589	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD1810	Approved
0.5882	Remote Similarity	NPD1811	Approved
0.5865	Remote Similarity	NPD6412	Phase 2
0.5833	Remote Similarity	NPD7983	Approved
0.5833	Remote Similarity	NPD1399	Approved
0.5833	Remote Similarity	NPD1400	Approved
0.5821	Remote Similarity	NPD8788	Approved
0.58	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4802	Phase 2
0.5795	Remote Similarity	NPD4238	Approved
0.5789	Remote Similarity	NPD3716	Discontinued
0.5789	Remote Similarity	NPD8328	Phase 3
0.5783	Remote Similarity	NPD8277	Approved
0.5752	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6940	Discontinued
0.5702	Remote Similarity	NPD8080	Discontinued
0.57	Remote Similarity	NPD881	Approved
0.5673	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD2270	Approved
0.5663	Remote Similarity	NPD8278	Approved
0.5652	Remote Similarity	NPD7830	Approved
0.5652	Remote Similarity	NPD7829	Approved
0.5648	Remote Similarity	NPD2690	Discontinued
0.5632	Remote Similarity	NPD376	Approved
0.5632	Remote Similarity	NPD11	Approved
0.563	Remote Similarity	NPD8392	Approved
0.563	Remote Similarity	NPD8390	Approved
0.563	Remote Similarity	NPD8391	Approved
0.5603	Remote Similarity	NPD8340	Approved
0.5603	Remote Similarity	NPD8341	Approved
0.5603	Remote Similarity	NPD8342	Approved
0.5603	Remote Similarity	NPD8299	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