NPASS Compound

Structure

NPC178548 OpenBabel07101719512D 43 47 0 0 1 0 0 0 0 0999 V2000 7.5802 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2274 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3004 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6554 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9403 -4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6531 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2493 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3223 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9621 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 1 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 6.0622 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6010 -1.0000 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 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2930 -5.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6010 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3223 0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 32 1 0 0 0 0 11 33 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 16 3 1 6 0 0 0 16 22 1 0 0 0 0 17 32 1 6 0 0 0 18 34 2 0 0 0 0 19 42 1 6 0 0 0 20 7 1 1 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 32 1 6 0 0 0 22 24 2 0 0 0 0 22 33 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 1 0 0 0 24 25 1 0 0 0 0 24 35 1 0 0 0 0 25 36 2 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 26 37 1 6 0 0 0 27 29 1 0 0 0 0 27 38 1 1 0 0 0 28 31 1 0 0 0 0 28 39 1 1 0 0 0 29 30 1 6 0 0 0 29 43 1 0 0 0 0 30 40 2 0 0 0 0 30 41 1 0 0 0 0 31 42 1 6 0 0 0 31 43 1 0 0 0 0 32 4 1 6 0 0 0 33 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	606.34
Volume:	613.898
LogP:	3.11
LogD:	2.57
LogS:	-4.361
# Rotatable Bonds:	8
TPSA:	167.66
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.238
Synthetic Accessibility Score:	5.328
Fsp3:	0.879
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.33
MDCK Permeability:	5.400877489591949e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.885
Human Intestinal Absorption (HIA):	0.462
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.523

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	89.83695983886719%
Volume Distribution (VD):	0.397
Pgp-substrate:	4.428019046783447%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.393
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	3.74
Half-life (T1/2):	0.649

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.456
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.714
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.244
Carcinogencity:	0.411
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.716

Download Data

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

Natural Product: NPC178548

Natural Product ID:	NPC178548
*Common Name:**	Pandaroside D
IUPAC Name:	(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3S,5S,8R,9S,10S,13S,14R)-16-hydroxy-10,13-dimethyl-17-[(2R)-6-methyl-4-oxoheptan-2-yl]-15-oxo-1,2,3,4,5,6,7,8,9,11,12,14-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid
Synonyms:	Pandaroside D
Standard InCHIKey:	CFFDFUDCYHFINU-HSSSCCAZSA-N
Standard InCHI:	InChI=1S/C33H50O10/c1-15(2)12-18(34)13-16(3)22-24(35)25(36)23-20-7-6-17-14-19(8-10-32(17,4)21(20)9-11-33(22,23)5)42-31-28(39)26(37)27(38)29(43-31)30(40)41/h15-17,19-21,23,26-29,31,35,37-39H,6-14H2,1-5H3,(H,40,41)/t16-,17+,19+,20-,21+,23+,26+,27+,28-,29+,31-,32+,33-/m1/s1
SMILES:	CC(C)CC(=O)C[C@@H](C)C1=C(C(=O)[C@@H]2[C@@H]3CC[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1214515
PubChem CID:	44191620
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0001447] Steroid glucuronide conjugates

*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
NPO20847	Pandaros acanthifolium	Species	Clathriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20614907]
NPO20847	Pandaros acanthifolium	Species	Clathriidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[23245401]
NPO20847	Pandaros acanthifolium	Species	Clathriidae	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	4
Others	1

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	96.6	uM	PMID[531417]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	15300.0	nM	PMID[531417]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	80800.0	nM	PMID[531417]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	31000.0	nM	PMID[531417]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	13500.0	nM	PMID[531417]

☑ 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 NPC178548 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	297
0.1-0.2	2031
0.2-0.3	5626
0.3-0.4	9419
0.4-0.5	11134
0.5-0.6	7416
0.6-0.7	4340
0.7-0.8	1848
0.8-0.85	434
0.85-0.9	131
0.9-0.95	9
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC258592
0.982	High Similarity	NPC258815
0.982	High Similarity	NPC194310
0.982	High Similarity	NPC169727
0.982	High Similarity	NPC258789
0.982	High Similarity	NPC47567
0.982	High Similarity	NPC241310
0.982	High Similarity	NPC131841
0.982	High Similarity	NPC412
0.9561	High Similarity	NPC469842
0.9561	High Similarity	NPC469841
0.9469	High Similarity	NPC187950
0.9469	High Similarity	NPC278163
0.9391	High Similarity	NPC177820
0.9391	High Similarity	NPC30188
0.9224	High Similarity	NPC7850
0.9224	High Similarity	NPC6615
0.8889	High Similarity	NPC471965
0.8824	High Similarity	NPC285091
0.8814	High Similarity	NPC14617
0.8814	High Similarity	NPC471964
0.8814	High Similarity	NPC202666
0.8814	High Similarity	NPC262199
0.8814	High Similarity	NPC471961
0.8793	High Similarity	NPC319570
0.8739	High Similarity	NPC247315
0.8739	High Similarity	NPC471962
0.8739	High Similarity	NPC471963
0.8718	High Similarity	NPC476849
0.8707	High Similarity	NPC286347
0.8707	High Similarity	NPC239293
0.8667	High Similarity	NPC87662
0.8632	High Similarity	NPC473884
0.8632	High Similarity	NPC35405
0.8632	High Similarity	NPC469945
0.8632	High Similarity	NPC11551
0.8632	High Similarity	NPC475171
0.8632	High Similarity	NPC157868
0.8632	High Similarity	NPC214484
0.8632	High Similarity	NPC472949
0.8632	High Similarity	NPC309780
0.8632	High Similarity	NPC6377
0.8632	High Similarity	NPC180550
0.8632	High Similarity	NPC208381
0.8632	High Similarity	NPC114441
0.8632	High Similarity	NPC39211
0.8621	High Similarity	NPC224121
0.8621	High Similarity	NPC477252
0.8596	High Similarity	NPC477253
0.8571	High Similarity	NPC107966
0.8571	High Similarity	NPC249848
0.8571	High Similarity	NPC40775
0.8571	High Similarity	NPC235438
0.8571	High Similarity	NPC162574
0.8559	High Similarity	NPC294112
0.8534	High Similarity	NPC173686
0.8534	High Similarity	NPC16081
0.8512	High Similarity	NPC47113
0.8512	High Similarity	NPC174367
0.85	High Similarity	NPC281148
0.85	High Similarity	NPC1980
0.85	High Similarity	NPC30735
0.85	High Similarity	NPC235405
0.85	High Similarity	NPC238005
0.85	High Similarity	NPC141196
0.8487	Intermediate Similarity	NPC470478
0.8487	Intermediate Similarity	NPC62725
0.8487	Intermediate Similarity	NPC223301
0.8487	Intermediate Similarity	NPC86222
0.8487	Intermediate Similarity	NPC301449
0.8487	Intermediate Similarity	NPC104372
0.8487	Intermediate Similarity	NPC75417
0.8487	Intermediate Similarity	NPC297263
0.8487	Intermediate Similarity	NPC171544
0.8487	Intermediate Similarity	NPC242840
0.8487	Intermediate Similarity	NPC31838
0.8487	Intermediate Similarity	NPC64715
0.8487	Intermediate Similarity	NPC22956
0.8487	Intermediate Similarity	NPC222580
0.8487	Intermediate Similarity	NPC159309
0.8487	Intermediate Similarity	NPC31193
0.8487	Intermediate Similarity	NPC114484
0.8487	Intermediate Similarity	NPC11242
0.8475	Intermediate Similarity	NPC127530
0.8455	Intermediate Similarity	NPC54614
0.8455	Intermediate Similarity	NPC309096
0.8448	Intermediate Similarity	NPC45218
0.8448	Intermediate Similarity	NPC268238
0.8448	Intermediate Similarity	NPC323821
0.8448	Intermediate Similarity	NPC143268
0.843	Intermediate Similarity	NPC130229
0.843	Intermediate Similarity	NPC470477
0.8417	Intermediate Similarity	NPC4749
0.8417	Intermediate Similarity	NPC236870
0.8417	Intermediate Similarity	NPC80986
0.8417	Intermediate Similarity	NPC21691
0.8417	Intermediate Similarity	NPC10607
0.8417	Intermediate Similarity	NPC187290
0.8417	Intermediate Similarity	NPC475591
0.8417	Intermediate Similarity	NPC275343
0.8417	Intermediate Similarity	NPC213952
0.8403	Intermediate Similarity	NPC236657
0.8403	Intermediate Similarity	NPC118440
0.839	Intermediate Similarity	NPC297179
0.8374	Intermediate Similarity	NPC295220
0.8374	Intermediate Similarity	NPC475636
0.8362	Intermediate Similarity	NPC73986
0.8361	Intermediate Similarity	NPC181066
0.8361	Intermediate Similarity	NPC469947
0.8361	Intermediate Similarity	NPC470218
0.8361	Intermediate Similarity	NPC198714
0.8347	Intermediate Similarity	NPC258617
0.8347	Intermediate Similarity	NPC227397
0.8347	Intermediate Similarity	NPC200049
0.8347	Intermediate Similarity	NPC478066
0.8347	Intermediate Similarity	NPC44716
0.8347	Intermediate Similarity	NPC2370
0.8347	Intermediate Similarity	NPC283417
0.8347	Intermediate Similarity	NPC302543
0.8347	Intermediate Similarity	NPC257211
0.8333	Intermediate Similarity	NPC302887
0.8333	Intermediate Similarity	NPC275675
0.8333	Intermediate Similarity	NPC187618
0.8333	Intermediate Similarity	NPC42675
0.8319	Intermediate Similarity	NPC473920
0.8319	Intermediate Similarity	NPC192791
0.8319	Intermediate Similarity	NPC232258
0.8306	Intermediate Similarity	NPC477196
0.8305	Intermediate Similarity	NPC309433
0.8305	Intermediate Similarity	NPC473304
0.8291	Intermediate Similarity	NPC472274
0.8291	Intermediate Similarity	NPC18547
0.8291	Intermediate Similarity	NPC474906
0.8279	Intermediate Similarity	NPC475194
0.8279	Intermediate Similarity	NPC33068
0.8279	Intermediate Similarity	NPC160452
0.8279	Intermediate Similarity	NPC318135
0.8276	Intermediate Similarity	NPC471967
0.8268	Intermediate Similarity	NPC262813
0.8264	Intermediate Similarity	NPC313110
0.8264	Intermediate Similarity	NPC131469
0.8264	Intermediate Similarity	NPC216866
0.825	Intermediate Similarity	NPC471406
0.824	Intermediate Similarity	NPC134914
0.824	Intermediate Similarity	NPC262796
0.824	Intermediate Similarity	NPC329993
0.824	Intermediate Similarity	NPC173435
0.824	Intermediate Similarity	NPC264566
0.824	Intermediate Similarity	NPC477197
0.824	Intermediate Similarity	NPC476074
0.824	Intermediate Similarity	NPC478155
0.824	Intermediate Similarity	NPC301639
0.824	Intermediate Similarity	NPC475377
0.824	Intermediate Similarity	NPC478065
0.824	Intermediate Similarity	NPC45346
0.824	Intermediate Similarity	NPC172374
0.824	Intermediate Similarity	NPC25998
0.824	Intermediate Similarity	NPC475167
0.824	Intermediate Similarity	NPC478064
0.8235	Intermediate Similarity	NPC176005
0.8235	Intermediate Similarity	NPC291564
0.8235	Intermediate Similarity	NPC109588
0.8226	Intermediate Similarity	NPC477193
0.8226	Intermediate Similarity	NPC477194
0.8226	Intermediate Similarity	NPC477191
0.8226	Intermediate Similarity	NPC477192
0.8226	Intermediate Similarity	NPC475281
0.8226	Intermediate Similarity	NPC329923
0.8226	Intermediate Similarity	NPC293623
0.8226	Intermediate Similarity	NPC477078
0.8226	Intermediate Similarity	NPC477075
0.8226	Intermediate Similarity	NPC168899
0.8226	Intermediate Similarity	NPC69273
0.822	Intermediate Similarity	NPC31797
0.822	Intermediate Similarity	NPC235539
0.822	Intermediate Similarity	NPC88945
0.822	Intermediate Similarity	NPC134869
0.822	Intermediate Similarity	NPC152199
0.8211	Intermediate Similarity	NPC475368
0.8211	Intermediate Similarity	NPC284449
0.8211	Intermediate Similarity	NPC104427
0.8211	Intermediate Similarity	NPC273962
0.8205	Intermediate Similarity	NPC255017
0.8205	Intermediate Similarity	NPC260665
0.8205	Intermediate Similarity	NPC62696
0.8205	Intermediate Similarity	NPC293038
0.8203	Intermediate Similarity	NPC251998
0.8203	Intermediate Similarity	NPC141215
0.8203	Intermediate Similarity	NPC471089
0.8203	Intermediate Similarity	NPC190065
0.819	Intermediate Similarity	NPC285410
0.819	Intermediate Similarity	NPC263827
0.819	Intermediate Similarity	NPC250481
0.819	Intermediate Similarity	NPC31839
0.819	Intermediate Similarity	NPC11035
0.819	Intermediate Similarity	NPC272242
0.8189	Intermediate Similarity	NPC478069
0.8182	Intermediate Similarity	NPC129434
0.8182	Intermediate Similarity	NPC202051
0.8175	Intermediate Similarity	NPC478152

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 NPC178548 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	2371
0.2-0.3	3845
0.3-0.4	1648
0.4-0.5	558
0.5-0.6	250
0.6-0.7	142
0.7-0.8	42
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8814	High Similarity	NPD8328	Phase 3
0.8783	High Similarity	NPD8295	Clinical (unspecified phase)
0.8374	Intermediate Similarity	NPD7736	Approved
0.8174	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8145	Intermediate Similarity	NPD8293	Discontinued
0.8016	Intermediate Similarity	NPD7319	Approved
0.7967	Intermediate Similarity	NPD6370	Approved
0.792	Intermediate Similarity	NPD7507	Approved
0.7845	Intermediate Similarity	NPD6412	Phase 2
0.784	Intermediate Similarity	NPD7492	Approved
0.7805	Intermediate Similarity	NPD6059	Approved
0.7805	Intermediate Similarity	NPD6319	Approved
0.7805	Intermediate Similarity	NPD6054	Approved
0.7778	Intermediate Similarity	NPD6616	Approved
0.7717	Intermediate Similarity	NPD7078	Approved
0.7667	Intermediate Similarity	NPD6882	Approved
0.7667	Intermediate Similarity	NPD8297	Approved
0.7627	Intermediate Similarity	NPD6686	Approved
0.7603	Intermediate Similarity	NPD8133	Approved
0.76	Intermediate Similarity	NPD6016	Approved
0.76	Intermediate Similarity	NPD6015	Approved
0.7563	Intermediate Similarity	NPD6373	Approved
0.7563	Intermediate Similarity	NPD6372	Approved
0.7561	Intermediate Similarity	NPD6009	Approved
0.754	Intermediate Similarity	NPD5988	Approved
0.7521	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6675	Approved
0.7458	Intermediate Similarity	NPD6402	Approved
0.7458	Intermediate Similarity	NPD7128	Approved
0.7458	Intermediate Similarity	NPD5739	Approved
0.7438	Intermediate Similarity	NPD6650	Approved
0.7438	Intermediate Similarity	NPD6649	Approved
0.7381	Intermediate Similarity	NPD8294	Approved
0.7381	Intermediate Similarity	NPD8377	Approved
0.736	Intermediate Similarity	NPD7328	Approved
0.736	Intermediate Similarity	NPD7327	Approved
0.7333	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6899	Approved
0.7333	Intermediate Similarity	NPD7320	Approved
0.7333	Intermediate Similarity	NPD6881	Approved
0.7323	Intermediate Similarity	NPD8033	Approved
0.7323	Intermediate Similarity	NPD8378	Approved
0.7323	Intermediate Similarity	NPD8380	Approved
0.7323	Intermediate Similarity	NPD8335	Approved
0.7323	Intermediate Similarity	NPD8296	Approved
0.7323	Intermediate Similarity	NPD8379	Approved
0.7317	Intermediate Similarity	NPD4632	Approved
0.7302	Intermediate Similarity	NPD7516	Approved
0.7295	Intermediate Similarity	NPD8130	Phase 1
0.7252	Intermediate Similarity	NPD6033	Approved
0.725	Intermediate Similarity	NPD5697	Approved
0.725	Intermediate Similarity	NPD5701	Approved
0.7213	Intermediate Similarity	NPD7290	Approved
0.7213	Intermediate Similarity	NPD6883	Approved
0.7213	Intermediate Similarity	NPD7102	Approved
0.7154	Intermediate Similarity	NPD6617	Approved
0.7154	Intermediate Similarity	NPD6869	Approved
0.7154	Intermediate Similarity	NPD6847	Approved
0.7132	Intermediate Similarity	NPD8080	Discontinued
0.7131	Intermediate Similarity	NPD6014	Approved
0.7131	Intermediate Similarity	NPD6013	Approved
0.7131	Intermediate Similarity	NPD6012	Approved
0.7077	Intermediate Similarity	NPD7604	Phase 2
0.7073	Intermediate Similarity	NPD4634	Approved
0.7054	Intermediate Similarity	NPD8513	Phase 3
0.7054	Intermediate Similarity	NPD8516	Approved
0.7054	Intermediate Similarity	NPD5983	Phase 2
0.7054	Intermediate Similarity	NPD8517	Approved
0.7054	Intermediate Similarity	NPD7503	Approved
0.7054	Intermediate Similarity	NPD8515	Approved
0.7049	Intermediate Similarity	NPD6011	Approved
0.7016	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7902	Approved
0.7009	Intermediate Similarity	NPD6083	Phase 2
0.7009	Intermediate Similarity	NPD6084	Phase 2
0.7008	Intermediate Similarity	NPD7115	Discovery
0.697	Remote Similarity	NPD6336	Discontinued
0.6923	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7748	Approved
0.687	Remote Similarity	NPD8034	Phase 2
0.687	Remote Similarity	NPD8035	Phase 2
0.6864	Remote Similarity	NPD4755	Approved
0.6855	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6399	Phase 3
0.6807	Remote Similarity	NPD5696	Approved
0.6807	Remote Similarity	NPD7638	Approved
0.68	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6274	Approved
0.6794	Remote Similarity	NPD6921	Approved
0.678	Remote Similarity	NPD4697	Phase 3
0.6769	Remote Similarity	NPD7101	Approved
0.6769	Remote Similarity	NPD7100	Approved
0.6754	Remote Similarity	NPD5737	Approved
0.6754	Remote Similarity	NPD6672	Approved
0.6752	Remote Similarity	NPD7900	Approved
0.6752	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4696	Approved
0.675	Remote Similarity	NPD4700	Approved
0.675	Remote Similarity	NPD5285	Approved
0.675	Remote Similarity	NPD7639	Approved
0.675	Remote Similarity	NPD5286	Approved
0.675	Remote Similarity	NPD7640	Approved
0.6748	Remote Similarity	NPD6008	Approved
0.6724	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD5328	Approved
0.6695	Remote Similarity	NPD5695	Phase 3
0.6692	Remote Similarity	NPD6067	Discontinued
0.6692	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD8171	Discontinued
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6642	Remote Similarity	NPD5956	Approved
0.6639	Remote Similarity	NPD5211	Phase 2
0.6639	Remote Similarity	NPD5221	Approved
0.6639	Remote Similarity	NPD5224	Approved
0.6639	Remote Similarity	NPD5222	Approved
0.6639	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7632	Discontinued
0.6639	Remote Similarity	NPD5225	Approved
0.6639	Remote Similarity	NPD4633	Approved
0.6639	Remote Similarity	NPD5226	Approved
0.6618	Remote Similarity	NPD8336	Approved
0.6618	Remote Similarity	NPD8337	Approved
0.6615	Remote Similarity	NPD6317	Approved
0.6615	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4767	Approved
0.6613	Remote Similarity	NPD4768	Approved
0.661	Remote Similarity	NPD5282	Discontinued
0.6585	Remote Similarity	NPD5175	Approved
0.6585	Remote Similarity	NPD5174	Approved
0.6583	Remote Similarity	NPD5173	Approved
0.6581	Remote Similarity	NPD6079	Approved
0.6565	Remote Similarity	NPD6313	Approved
0.6565	Remote Similarity	NPD6314	Approved
0.656	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5223	Approved
0.6538	Remote Similarity	NPD6940	Discontinued
0.6532	Remote Similarity	NPD5141	Approved
0.6529	Remote Similarity	NPD4225	Approved
0.6508	Remote Similarity	NPD4730	Approved
0.6508	Remote Similarity	NPD4729	Approved
0.6491	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4754	Approved
0.6441	Remote Similarity	NPD6411	Approved
0.6435	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD8338	Approved
0.6423	Remote Similarity	NPD8074	Phase 3
0.642	Remote Similarity	NPD7799	Discontinued
0.6418	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6080	Approved
0.641	Remote Similarity	NPD6673	Approved
0.641	Remote Similarity	NPD6904	Approved
0.641	Remote Similarity	NPD4753	Phase 2
0.641	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6371	Approved
0.6406	Remote Similarity	NPD5250	Approved
0.6406	Remote Similarity	NPD5248	Approved
0.6406	Remote Similarity	NPD5247	Approved
0.6406	Remote Similarity	NPD5249	Phase 3
0.6406	Remote Similarity	NPD5251	Approved
0.64	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5128	Approved
0.6364	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD7260	Phase 2
0.6319	Remote Similarity	NPD6333	Approved
0.6319	Remote Similarity	NPD6334	Approved
0.6312	Remote Similarity	NPD6845	Suspended
0.6308	Remote Similarity	NPD6053	Discontinued
0.6306	Remote Similarity	NPD6115	Approved
0.6306	Remote Similarity	NPD6114	Approved
0.6306	Remote Similarity	NPD3617	Approved
0.6306	Remote Similarity	NPD6697	Approved
0.6306	Remote Similarity	NPD6118	Approved
0.6303	Remote Similarity	NPD7983	Approved
0.6293	Remote Similarity	NPD6409	Approved
0.6293	Remote Similarity	NPD7334	Approved
0.6293	Remote Similarity	NPD5330	Approved
0.6293	Remote Similarity	NPD6684	Approved
0.6293	Remote Similarity	NPD7146	Approved
0.6293	Remote Similarity	NPD7521	Approved
0.629	Remote Similarity	NPD1700	Approved
0.6281	Remote Similarity	NPD5210	Approved
0.6281	Remote Similarity	NPD4629	Approved
0.6271	Remote Similarity	NPD6101	Approved
0.6271	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD4202	Approved
0.6239	Remote Similarity	NPD3573	Approved
0.6231	Remote Similarity	NPD5215	Approved
0.6231	Remote Similarity	NPD5216	Approved
0.6231	Remote Similarity	NPD5217	Approved
0.6218	Remote Similarity	NPD6698	Approved
0.6218	Remote Similarity	NPD46	Approved
0.6216	Remote Similarity	NPD6116	Phase 1
0.6194	Remote Similarity	NPD7641	Discontinued

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