NPASS Compound

Structure

NPC475621 OpenBabel07101719502D 47 52 0 0 1 0 0 0 0 0999 V2000 5.1093 1.9116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0154 5.2207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9323 1.4310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2905 0.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5899 -1.8263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2905 5.2207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4479 -0.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8153 0.3246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1558 -1.2772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8905 0.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2310 -1.4738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8341 -0.9248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6529 -0.4521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0154 0.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8208 -0.0988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4960 0.8637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5146 -2.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2905 2.3843 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8341 4.7479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5984 -0.7711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0154 -0.4521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4363 0.7649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8992 -1.5574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6529 0.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8341 0.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2651 -0.8637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9403 0.0988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4256 -2.3223 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3248 -0.7649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2905 3.3298 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4717 3.8025 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6529 3.3298 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6529 2.3843 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6222 -1.3975 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1966 -0.9248 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6529 5.2207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0583 -3.0249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1093 3.8025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4410 -1.8702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9920 1.5298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4717 0.9661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6497 -1.7274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4717 4.7479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4717 1.9116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8341 3.8025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8341 1.9116 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 2 19 1 0 0 0 0 3 40 1 0 0 0 0 4 41 1 0 0 0 0 5 42 1 0 0 0 0 6 43 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 20 2 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 21 1 0 0 0 0 13 24 1 0 0 0 0 14 21 2 0 0 0 0 14 25 1 0 0 0 0 15 22 2 0 0 0 0 15 26 1 0 0 0 0 16 22 1 0 0 0 0 16 27 2 0 0 0 0 17 23 1 0 0 0 0 17 28 1 0 0 0 0 18 1 1 1 0 0 0 18 30 1 0 0 0 0 18 44 1 0 0 0 0 19 36 2 0 0 0 0 19 45 1 0 0 0 0 20 23 1 0 0 0 0 22 40 1 0 0 0 0 23 35 1 6 0 0 0 24 25 2 0 0 0 0 24 41 1 0 0 0 0 25 46 1 0 0 0 0 26 29 2 0 0 0 0 26 42 1 0 0 0 0 27 29 1 0 0 0 0 27 47 1 0 0 0 0 28 34 1 1 0 0 0 28 37 1 0 0 0 0 29 34 1 0 0 0 0 30 31 1 0 0 0 0 30 38 1 6 0 0 0 31 32 1 0 0 0 0 31 43 1 1 0 0 0 32 33 1 0 0 0 0 32 45 1 1 0 0 0 33 44 1 0 0 0 0 33 46 1 1 0 0 0 34 35 1 6 0 0 0 34 39 1 0 0 0 0 35 21 1 6 0 0 0 35 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	652.25
Volume:	641.695
LogP:	3.343
LogD:	2.865
LogS:	-4.813
# Rotatable Bonds:	10
TPSA:	151.6
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	4.79
Fsp3:	0.457
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:	-5.586
MDCK Permeability:	5.408965807873756e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.686

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	76.7406234741211%
Volume Distribution (VD):	0.472
Pgp-substrate:	13.93895149230957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.264
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.172
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.199
CYP2D6-substrate:	0.741
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.789

ADMET: Excretion

Clearance (CL):	8.528
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.78
Human Hepatotoxicity (H-HT):	0.841
Drug-inuced Liver Injury (DILI):	0.832
AMES Toxicity:	0.391
Rat Oral Acute Toxicity:	0.151
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.035
Carcinogencity:	0.07
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.8

Download Data

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

Natural Product: NPC475621

Natural Product ID:	NPC475621
*Common Name:**	11-Alpha-(2'-Acetoxy-3'-Methoxyrhamnosyl)-Rocaglaol
IUPAC Name:	[(2S,3S,4S,5R,6R)-2-[5-[(1R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-3a-yl]-2-methoxyphenoxy]-5-hydroxy-4-methoxy-6-methyloxan-3-yl] acetate
Synonyms:
Standard InCHIKey:	QKVLYKATVKEUOR-NAQGKKNMSA-N
Standard InCHI:	InChI=1S/C35H40O12/c1-18-30(38)31(43-6)32(45-19(2)36)33(44-18)46-25-14-21(12-13-24(25)41-4)35-23(20-10-8-7-9-11-20)17-28(37)34(35,39)29-26(42-5)15-22(40-3)16-27(29)47-35/h7-16,18,23,28,30-33,37-39H,17H2,1-6H3/t18-,23+,28-,30-,31+,32+,33+,34-,35+/m1/s1
SMILES:	CO[C@@H]1[C@H](OC(=O)C)[C@@H](O[C@@H]([C@H]1O)C)Oc1cc(ccc1OC)[C@]12Oc3c([C@]2(O)[C@@H](C[C@H]1c1ccccc1)O)c(OC)cc(c3)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509452
PubChem CID:	10794346
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene 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
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785416]
NPO6039	Aglaia laxiflora	Species	Meliaceae	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
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	0.0022	ml	PMID[552623]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.036	ml	PMID[552623]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.0042	ml	PMID[552623]

☑ 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 NPC475621 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	384
0.1-0.2	1502
0.2-0.3	3446
0.3-0.4	8071
0.4-0.5	10019
0.5-0.6	6516
0.6-0.7	8263
0.7-0.8	4028
0.8-0.85	398
0.85-0.9	62
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9241	High Similarity	NPC189730
0.9177	High Similarity	NPC164152
0.9085	High Similarity	NPC208818
0.9036	High Similarity	NPC149502
0.9036	High Similarity	NPC222665
0.9036	High Similarity	NPC271755
0.9036	High Similarity	NPC254071
0.8988	High Similarity	NPC23593
0.8987	High Similarity	NPC302610
0.8929	High Similarity	NPC107739
0.891	High Similarity	NPC20360
0.8882	High Similarity	NPC236089
0.8876	High Similarity	NPC263955
0.8824	High Similarity	NPC29587
0.8795	High Similarity	NPC59516
0.8773	High Similarity	NPC173726
0.8773	High Similarity	NPC241600
0.8773	High Similarity	NPC478269
0.8765	High Similarity	NPC11411
0.8734	High Similarity	NPC270751
0.8679	High Similarity	NPC35877
0.8679	High Similarity	NPC55158
0.8679	High Similarity	NPC51328
0.8679	High Similarity	NPC286235
0.8679	High Similarity	NPC95392
0.8679	High Similarity	NPC55715
0.8671	High Similarity	NPC39657
0.8667	High Similarity	NPC478267
0.8654	High Similarity	NPC184607
0.8634	High Similarity	NPC478268
0.8625	High Similarity	NPC472709
0.8625	High Similarity	NPC472710
0.8625	High Similarity	NPC147224
0.8625	High Similarity	NPC238140
0.8623	High Similarity	NPC222531
0.8616	High Similarity	NPC130449
0.8616	High Similarity	NPC248132
0.8606	High Similarity	NPC478265
0.859	High Similarity	NPC470937
0.858	High Similarity	NPC150442
0.8554	High Similarity	NPC149873
0.8554	High Similarity	NPC7191
0.8553	High Similarity	NPC320671
0.8553	High Similarity	NPC327412
0.8553	High Similarity	NPC328567
0.8553	High Similarity	NPC320970
0.8544	High Similarity	NPC181615
0.8544	High Similarity	NPC475096
0.8544	High Similarity	NPC43508
0.8544	High Similarity	NPC476301
0.8537	High Similarity	NPC478248
0.8521	High Similarity	NPC286809
0.8519	High Similarity	NPC233467
0.8519	High Similarity	NPC169404
0.8519	High Similarity	NPC53587
0.8519	High Similarity	NPC472612
0.8519	High Similarity	NPC59692
0.8519	High Similarity	NPC289967
0.8519	High Similarity	NPC176186
0.8519	High Similarity	NPC472611
0.8509	High Similarity	NPC475224
0.8509	High Similarity	NPC98624
0.85	High Similarity	NPC308178
0.85	High Similarity	NPC93924
0.8494	Intermediate Similarity	NPC73422
0.8494	Intermediate Similarity	NPC310399
0.8491	Intermediate Similarity	NPC99515
0.8491	Intermediate Similarity	NPC162193
0.8491	Intermediate Similarity	NPC276753
0.8491	Intermediate Similarity	NPC212890
0.8491	Intermediate Similarity	NPC205796
0.8491	Intermediate Similarity	NPC324492
0.8491	Intermediate Similarity	NPC93610
0.8491	Intermediate Similarity	NPC190714
0.8491	Intermediate Similarity	NPC241846
0.8491	Intermediate Similarity	NPC112861
0.8491	Intermediate Similarity	NPC317053
0.8491	Intermediate Similarity	NPC125755
0.8485	Intermediate Similarity	NPC125495
0.8481	Intermediate Similarity	NPC471667
0.8481	Intermediate Similarity	NPC79429
0.8481	Intermediate Similarity	NPC187774
0.8481	Intermediate Similarity	NPC471063
0.8481	Intermediate Similarity	NPC217635
0.8481	Intermediate Similarity	NPC472712
0.8481	Intermediate Similarity	NPC129417
0.8481	Intermediate Similarity	NPC283995
0.8481	Intermediate Similarity	NPC473046
0.8481	Intermediate Similarity	NPC470235
0.8481	Intermediate Similarity	NPC118385
0.8481	Intermediate Similarity	NPC472713
0.8471	Intermediate Similarity	NPC302506
0.8471	Intermediate Similarity	NPC287124
0.8471	Intermediate Similarity	NPC246947
0.8466	Intermediate Similarity	NPC78809
0.8457	Intermediate Similarity	NPC478249
0.8457	Intermediate Similarity	NPC324517
0.8457	Intermediate Similarity	NPC269914
0.8457	Intermediate Similarity	NPC329343
0.8457	Intermediate Similarity	NPC321972
0.8447	Intermediate Similarity	NPC106138
0.8443	Intermediate Similarity	NPC100465
0.8443	Intermediate Similarity	NPC115624
0.8443	Intermediate Similarity	NPC152424
0.8443	Intermediate Similarity	NPC90336
0.8438	Intermediate Similarity	NPC213074
0.8438	Intermediate Similarity	NPC99183
0.8438	Intermediate Similarity	NPC31325
0.8438	Intermediate Similarity	NPC227902
0.8438	Intermediate Similarity	NPC224674
0.8438	Intermediate Similarity	NPC275284
0.8438	Intermediate Similarity	NPC15956
0.8438	Intermediate Similarity	NPC193473
0.8438	Intermediate Similarity	NPC114505
0.8434	Intermediate Similarity	NPC209473
0.8434	Intermediate Similarity	NPC230531
0.8434	Intermediate Similarity	NPC329743
0.8434	Intermediate Similarity	NPC215400
0.8428	Intermediate Similarity	NPC279298
0.8428	Intermediate Similarity	NPC277867
0.8428	Intermediate Similarity	NPC161700
0.8428	Intermediate Similarity	NPC477702
0.8428	Intermediate Similarity	NPC18979
0.8428	Intermediate Similarity	NPC22150
0.8428	Intermediate Similarity	NPC38041
0.8424	Intermediate Similarity	NPC228357
0.8418	Intermediate Similarity	NPC470950
0.8418	Intermediate Similarity	NPC46092
0.8418	Intermediate Similarity	NPC81638
0.8418	Intermediate Similarity	NPC185307
0.8415	Intermediate Similarity	NPC159922
0.8415	Intermediate Similarity	NPC473425
0.8408	Intermediate Similarity	NPC108674
0.8405	Intermediate Similarity	NPC476352
0.8405	Intermediate Similarity	NPC474442
0.8405	Intermediate Similarity	NPC21902
0.8405	Intermediate Similarity	NPC215060
0.8405	Intermediate Similarity	NPC470264
0.8395	Intermediate Similarity	NPC145979
0.8395	Intermediate Similarity	NPC229882
0.8395	Intermediate Similarity	NPC158635
0.8395	Intermediate Similarity	NPC260781
0.8395	Intermediate Similarity	NPC214326
0.8395	Intermediate Similarity	NPC218041
0.8395	Intermediate Similarity	NPC24425
0.8395	Intermediate Similarity	NPC182368
0.8395	Intermediate Similarity	NPC225815
0.8395	Intermediate Similarity	NPC473989
0.8395	Intermediate Similarity	NPC469706
0.8395	Intermediate Similarity	NPC469707
0.8395	Intermediate Similarity	NPC185955
0.8395	Intermediate Similarity	NPC9933
0.8385	Intermediate Similarity	NPC316676
0.8385	Intermediate Similarity	NPC175976
0.8385	Intermediate Similarity	NPC226153
0.8385	Intermediate Similarity	NPC252402
0.8385	Intermediate Similarity	NPC102934
0.8385	Intermediate Similarity	NPC166584
0.8385	Intermediate Similarity	NPC325720
0.8385	Intermediate Similarity	NPC304048
0.8385	Intermediate Similarity	NPC301961
0.8383	Intermediate Similarity	NPC100936
0.8383	Intermediate Similarity	NPC1253
0.8375	Intermediate Similarity	NPC260397
0.8375	Intermediate Similarity	NPC87794
0.8375	Intermediate Similarity	NPC211758
0.8365	Intermediate Similarity	NPC473045
0.8365	Intermediate Similarity	NPC114119
0.8365	Intermediate Similarity	NPC168579
0.8365	Intermediate Similarity	NPC141569
0.8365	Intermediate Similarity	NPC471415
0.8365	Intermediate Similarity	NPC470097
0.8365	Intermediate Similarity	NPC138227
0.8365	Intermediate Similarity	NPC25292
0.8365	Intermediate Similarity	NPC469313
0.8365	Intermediate Similarity	NPC477701
0.8365	Intermediate Similarity	NPC179521
0.8365	Intermediate Similarity	NPC76176
0.8365	Intermediate Similarity	NPC166884
0.8365	Intermediate Similarity	NPC84181
0.8354	Intermediate Similarity	NPC469559
0.8354	Intermediate Similarity	NPC476356
0.8354	Intermediate Similarity	NPC299706
0.8354	Intermediate Similarity	NPC478241
0.8354	Intermediate Similarity	NPC89693
0.8354	Intermediate Similarity	NPC472714
0.8354	Intermediate Similarity	NPC475084
0.8354	Intermediate Similarity	NPC229548
0.8354	Intermediate Similarity	NPC61604
0.8354	Intermediate Similarity	NPC5262
0.8354	Intermediate Similarity	NPC245615
0.8354	Intermediate Similarity	NPC115466
0.8354	Intermediate Similarity	NPC189115
0.8354	Intermediate Similarity	NPC472353
0.8353	Intermediate Similarity	NPC306475
0.8344	Intermediate Similarity	NPC226547
0.8344	Intermediate Similarity	NPC224472
0.8344	Intermediate Similarity	NPC473621
0.8343	Intermediate Similarity	NPC14294
0.8343	Intermediate Similarity	NPC116759

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 NPC475621 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	853
0.2-0.3	1897
0.3-0.4	2746
0.4-0.5	1891
0.5-0.6	985
0.6-0.7	410
0.7-0.8	59
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD7199	Phase 2
0.8452	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7228	Approved
0.8204	Intermediate Similarity	NPD4966	Approved
0.8204	Intermediate Similarity	NPD4965	Approved
0.8204	Intermediate Similarity	NPD4967	Phase 2
0.8133	Intermediate Similarity	NPD37	Approved
0.8114	Intermediate Similarity	NPD7685	Pre-registration
0.8107	Intermediate Similarity	NPD6234	Discontinued
0.8011	Intermediate Similarity	NPD7240	Approved
0.8	Intermediate Similarity	NPD1653	Approved
0.784	Intermediate Similarity	NPD6674	Discontinued
0.7833	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7074	Phase 3
0.7785	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1613	Approved
0.7765	Intermediate Similarity	NPD8455	Phase 2
0.774	Intermediate Similarity	NPD7054	Approved
0.7716	Intermediate Similarity	NPD7266	Discontinued
0.7697	Intermediate Similarity	NPD7472	Approved
0.7684	Intermediate Similarity	NPD3818	Discontinued
0.7674	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7808	Phase 3
0.7643	Intermediate Similarity	NPD4908	Phase 1
0.7607	Intermediate Similarity	NPD5763	Approved
0.7607	Intermediate Similarity	NPD5762	Approved
0.7595	Intermediate Similarity	NPD3027	Phase 3
0.7592	Intermediate Similarity	NPD7680	Approved
0.7569	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5844	Phase 1
0.7532	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7251	Discontinued
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7474	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6166	Phase 2
0.7472	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6797	Phase 2
0.7429	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7549	Discontinued
0.7363	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6653	Approved
0.7358	Intermediate Similarity	NPD2861	Phase 2
0.7348	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7097	Phase 1
0.7308	Intermediate Similarity	NPD1091	Approved
0.7301	Intermediate Similarity	NPD5735	Approved
0.7301	Intermediate Similarity	NPD5124	Phase 1
0.7301	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1934	Approved
0.7289	Intermediate Similarity	NPD6005	Phase 3
0.7289	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6004	Phase 3
0.7289	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6002	Phase 3
0.7243	Intermediate Similarity	NPD8313	Approved
0.7243	Intermediate Similarity	NPD8312	Approved
0.7239	Intermediate Similarity	NPD4140	Approved
0.7232	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3817	Phase 2
0.7204	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1610	Phase 2
0.7195	Intermediate Similarity	NPD6355	Discontinued
0.7184	Intermediate Similarity	NPD7028	Phase 2
0.7167	Intermediate Similarity	NPD3787	Discontinued
0.7159	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7134	Intermediate Similarity	NPD3620	Phase 2
0.7134	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1652	Phase 2
0.7089	Intermediate Similarity	NPD3705	Approved
0.7076	Intermediate Similarity	NPD5058	Phase 3
0.7072	Intermediate Similarity	NPD7229	Phase 3
0.7072	Intermediate Similarity	NPD6232	Discontinued
0.7068	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1465	Phase 2
0.7062	Intermediate Similarity	NPD7819	Suspended
0.7055	Intermediate Similarity	NPD7095	Approved
0.7039	Intermediate Similarity	NPD7075	Discontinued
0.7012	Intermediate Similarity	NPD6798	Discontinued
0.7011	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD6843	Phase 3
0.7	Intermediate Similarity	NPD6841	Approved
0.7	Intermediate Similarity	NPD6842	Approved
0.7	Intermediate Similarity	NPD4749	Approved
0.6983	Remote Similarity	NPD3882	Suspended
0.6983	Remote Similarity	NPD7768	Phase 2
0.6966	Remote Similarity	NPD2801	Approved
0.6966	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7033	Discontinued
0.6963	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4110	Phase 3
0.6959	Remote Similarity	NPD7466	Approved
0.6951	Remote Similarity	NPD4625	Phase 3
0.6949	Remote Similarity	NPD7411	Suspended
0.6949	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6353	Approved
0.6933	Remote Similarity	NPD3018	Phase 2
0.6927	Remote Similarity	NPD5402	Approved
0.6901	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1357	Approved
0.6893	Remote Similarity	NPD4380	Phase 2
0.6867	Remote Similarity	NPD6233	Phase 2
0.686	Remote Similarity	NPD3892	Phase 2
0.6857	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6273	Approved
0.6836	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1548	Phase 1
0.6833	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6100	Approved
0.6824	Remote Similarity	NPD6099	Approved
0.6823	Remote Similarity	NPD7906	Approved
0.6821	Remote Similarity	NPD6190	Approved
0.6818	Remote Similarity	NPD5403	Approved
0.6816	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6801	Discontinued
0.6814	Remote Similarity	NPD7783	Phase 2
0.6814	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3094	Phase 2
0.681	Remote Similarity	NPD6362	Approved
0.68	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7447	Phase 1
0.6798	Remote Similarity	NPD8151	Discontinued
0.679	Remote Similarity	NPD2982	Phase 2
0.679	Remote Similarity	NPD5327	Phase 3
0.679	Remote Similarity	NPD2983	Phase 2
0.677	Remote Similarity	NPD422	Phase 1
0.6763	Remote Similarity	NPD3750	Approved
0.6763	Remote Similarity	NPD4628	Phase 3
0.6761	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD3749	Approved
0.6754	Remote Similarity	NPD8054	Approved
0.6754	Remote Similarity	NPD8053	Approved
0.6748	Remote Similarity	NPD8651	Approved
0.6743	Remote Similarity	NPD7213	Phase 3
0.6743	Remote Similarity	NPD1511	Approved
0.6743	Remote Similarity	NPD7212	Phase 2
0.6742	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6959	Discontinued
0.6738	Remote Similarity	NPD7799	Discontinued
0.6731	Remote Similarity	NPD5283	Phase 1
0.6728	Remote Similarity	NPD2981	Phase 2
0.6715	Remote Similarity	NPD7930	Approved
0.6706	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5401	Approved
0.6703	Remote Similarity	NPD3051	Approved
0.6686	Remote Similarity	NPD1375	Discontinued
0.6685	Remote Similarity	NPD5761	Phase 2
0.6685	Remote Similarity	NPD5760	Phase 2
0.6684	Remote Similarity	NPD4663	Approved
0.6684	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD5588	Approved
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2970	Approved
0.6667	Remote Similarity	NPD2969	Approved
0.6667	Remote Similarity	NPD7843	Approved
0.6648	Remote Similarity	NPD6799	Approved
0.6648	Remote Similarity	NPD7458	Discontinued
0.6647	Remote Similarity	NPD2424	Discontinued
0.6646	Remote Similarity	NPD7157	Approved
0.6634	Remote Similarity	NPD7435	Discontinued
0.6631	Remote Similarity	NPD4481	Phase 3
0.663	Remote Similarity	NPD3382	Approved
0.663	Remote Similarity	NPD3384	Approved
0.663	Remote Similarity	NPD3383	Approved
0.6627	Remote Similarity	NPD5736	Approved
0.6618	Remote Similarity	NPD7583	Approved
0.6615	Remote Similarity	NPD7313	Approved
0.6615	Remote Similarity	NPD7312	Approved
0.6615	Remote Similarity	NPD7310	Approved
0.6615	Remote Similarity	NPD4577	Approved
0.6615	Remote Similarity	NPD7311	Approved
0.6615	Remote Similarity	NPD4578	Approved
0.6614	Remote Similarity	NPD8156	Discontinued
0.6611	Remote Similarity	NPD6599	Discontinued
0.661	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5177	Phase 3
0.6609	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4538	Approved
0.6608	Remote Similarity	NPD4536	Approved
0.6606	Remote Similarity	NPD2797	Approved
0.6593	Remote Similarity	NPD2977	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