NPASS Compound

Structure

NPC473469 OpenBabel07101718322D 51 56 0 0 1 0 0 0 0 0999 V2000 8.3614 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7141 4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4344 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7350 -3.9641 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 4.7894 0.9135 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 7.0743 3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0961 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 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 6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3833 4.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4562 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2350 -3.0981 0.0000 C 0 0 1 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 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7871 2.0032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7350 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2350 -3.0981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7350 -2.2321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2350 -1.3660 0.0000 C 0 0 2 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 8.2350 -1.3660 0.0000 C 0 0 1 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 5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8089 1.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7350 -3.9641 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 10.7350 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7350 -0.5000 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 7.7350 -2.2321 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 7.7350 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 8 11 1 0 0 0 0 8 17 2 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 11 26 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 38 1 0 0 0 0 14 21 1 0 0 0 0 14 22 1 0 0 0 0 15 22 1 0 0 0 0 15 28 1 0 0 0 0 16 25 1 0 0 0 0 16 27 1 0 0 0 0 18 3 1 1 0 0 0 18 26 1 0 0 0 0 18 29 1 0 0 0 0 19 4 1 6 0 0 0 19 30 1 0 0 0 0 19 48 1 0 0 0 0 20 5 1 1 0 0 0 20 31 1 0 0 0 0 20 49 1 0 0 0 0 21 39 1 1 0 0 0 22 40 1 1 0 0 0 23 10 1 6 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 24 39 1 1 0 0 0 25 38 1 1 0 0 0 26 41 1 1 0 0 0 27 29 1 0 0 0 0 27 50 1 1 0 0 0 28 39 1 1 0 0 0 28 51 1 0 0 0 0 29 38 1 1 0 0 0 30 32 1 0 0 0 0 30 42 1 1 0 0 0 31 33 1 0 0 0 0 31 43 1 6 0 0 0 32 34 1 0 0 0 0 32 44 1 6 0 0 0 33 35 1 0 0 0 0 33 45 1 1 0 0 0 34 36 1 0 0 0 0 34 46 1 6 0 0 0 35 37 1 0 0 0 0 35 47 1 1 0 0 0 36 48 1 0 0 0 0 36 50 1 1 0 0 0 37 49 1 0 0 0 0 37 51 1 6 0 0 0 38 6 1 1 0 0 0 39 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	726.46
Volume:	734.607
LogP:	4.416
LogD:	3.439
LogS:	-4.369
# Rotatable Bonds:	8
TPSA:	198.76
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.17
Synthetic Accessibility Score:	5.945
Fsp3:	0.949
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:	-6.08
MDCK Permeability:	0.00017246710194740444
Pgp-inhibitor:	0.884
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.932
20% Bioavailability (F20%):	0.273
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	70.54706573486328%
Volume Distribution (VD):	0.37
Pgp-substrate:	12.556894302368164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.541
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	2.566
Half-life (T1/2):	0.565

ADMET: Toxicity

hERG Blockers:	0.929
Human Hepatotoxicity (H-HT):	0.309
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.13
Skin Sensitization:	0.909
Carcinogencity:	0.186
Eye Corrosion:	0.005
Eye Irritation:	0.012
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC473469

Natural Product ID:	NPC473469
*Common Name:**	(22S)-16Beta-[(Alpha-L-Rhamnopyranosyl)Oxy]-3Beta,22-Dihydroxycholest-24-En-1Beta-Yl Alpha-L-Rhamnopyranoside
IUPAC Name:	(2R,3R,4R,5R,6S)-2-[[(1R,3R,5S,8S,9S,10S,13S,14S,16S,17R)-3-hydroxy-17-[(2S,3S)-3-hydroxy-6-methylhept-5-en-2-yl]-10,13-dimethyl-1-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl]oxy]-6-methyloxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	BAWUURNLFXGLTO-FIHIGEQISA-N
Standard InCHI:	InChI=1S/C39H66O12/c1-17(2)8-11-26(41)18(3)29-27(50-36-34(46)32(44)30(42)19(4)48-36)16-25-23-10-9-21-14-22(40)15-28(39(21,7)24(23)12-13-38(25,29)6)51-37-35(47)33(45)31(43)20(5)49-37/h8,18-37,40-47H,9-16H2,1-7H3/t18-,19+,20+,21+,22-,23-,24+,25+,26+,27+,28-,29+,30+,31+,32-,33-,34-,35-,36+,37+,38+,39+/m1/s1
SMILES:	CC(=CC[C@@H]([C@H]([C@H]1[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)[C@@H](C[C@@H](C2)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL442639
PubChem CID:	11399918
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal 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
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[12398536]
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	n.a.	bulb	n.a.	PMID[12398536]
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[15497941]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[559982]
NPT924	Cell Line	HSC-2	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[559982]

☑ 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 NPC473469 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	285
0.1-0.2	2064
0.2-0.3	6370
0.3-0.4	13409
0.4-0.5	9318
0.5-0.6	5294
0.6-0.7	3284
0.7-0.8	1497
0.8-0.85	728
0.85-0.9	241
0.9-0.95	181
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.97	High Similarity	NPC7213
0.9697	High Similarity	NPC473476
0.9697	High Similarity	NPC242748
0.9697	High Similarity	NPC473923
0.9592	High Similarity	NPC312553
0.9592	High Similarity	NPC159036
0.9592	High Similarity	NPC288694
0.9505	High Similarity	NPC476539
0.9505	High Similarity	NPC476540
0.9505	High Similarity	NPC476538
0.9505	High Similarity	NPC476541
0.9495	High Similarity	NPC245280
0.9495	High Similarity	NPC157659
0.9495	High Similarity	NPC189852
0.9495	High Similarity	NPC16520
0.9495	High Similarity	NPC16573
0.9495	High Similarity	NPC473020
0.9495	High Similarity	NPC286969
0.9495	High Similarity	NPC114874
0.9495	High Similarity	NPC211879
0.9495	High Similarity	NPC31907
0.9495	High Similarity	NPC131479
0.9495	High Similarity	NPC472252
0.9495	High Similarity	NPC155010
0.9495	High Similarity	NPC8039
0.9495	High Similarity	NPC120123
0.9417	High Similarity	NPC114188
0.9412	High Similarity	NPC306131
0.9412	High Similarity	NPC477026
0.9412	High Similarity	NPC477027
0.9412	High Similarity	NPC70204
0.9412	High Similarity	NPC475670
0.94	High Similarity	NPC187400
0.94	High Similarity	NPC165033
0.94	High Similarity	NPC221562
0.94	High Similarity	NPC470885
0.94	High Similarity	NPC273879
0.94	High Similarity	NPC475521
0.9394	High Similarity	NPC136816
0.9388	High Similarity	NPC473200
0.9388	High Similarity	NPC7341
0.9307	High Similarity	NPC152584
0.9307	High Similarity	NPC127801
0.9307	High Similarity	NPC160816
0.9307	High Similarity	NPC208477
0.9307	High Similarity	NPC194842
0.9307	High Similarity	NPC474569
0.9307	High Similarity	NPC269627
0.9307	High Similarity	NPC69737
0.9307	High Similarity	NPC181845
0.9307	High Similarity	NPC208594
0.93	High Similarity	NPC473198
0.9293	High Similarity	NPC129372
0.9293	High Similarity	NPC88000
0.9293	High Similarity	NPC472023
0.9293	High Similarity	NPC160734
0.9293	High Similarity	NPC4831
0.9293	High Similarity	NPC47566
0.9293	High Similarity	NPC309425
0.9286	High Similarity	NPC234287
0.9286	High Similarity	NPC280825
0.9238	High Similarity	NPC476693
0.9231	High Similarity	NPC13190
0.9231	High Similarity	NPC197231
0.9231	High Similarity	NPC475247
0.9231	High Similarity	NPC294129
0.9216	High Similarity	NPC226642
0.9216	High Similarity	NPC190395
0.9216	High Similarity	NPC234160
0.9216	High Similarity	NPC161676
0.9216	High Similarity	NPC63368
0.9216	High Similarity	NPC470432
0.9216	High Similarity	NPC113044
0.9216	High Similarity	NPC231340
0.9216	High Similarity	NPC230507
0.9216	High Similarity	NPC14704
0.9216	High Similarity	NPC181467
0.9216	High Similarity	NPC208650
0.9216	High Similarity	NPC14946
0.9216	High Similarity	NPC94272
0.9216	High Similarity	NPC283829
0.9216	High Similarity	NPC305423
0.9208	High Similarity	NPC312774
0.9208	High Similarity	NPC475365
0.92	High Similarity	NPC272015
0.9192	High Similarity	NPC282669
0.9184	High Similarity	NPC76486
0.9143	High Similarity	NPC19888
0.9143	High Similarity	NPC112274
0.9143	High Similarity	NPC475312
0.9126	High Similarity	NPC159005
0.9126	High Similarity	NPC246124
0.9126	High Similarity	NPC180183
0.9126	High Similarity	NPC472896
0.9126	High Similarity	NPC472897
0.9126	High Similarity	NPC295980
0.9126	High Similarity	NPC6931
0.9126	High Similarity	NPC220427
0.9126	High Similarity	NPC475634
0.9126	High Similarity	NPC98696
0.9126	High Similarity	NPC38217
0.9126	High Similarity	NPC472988
0.9118	High Similarity	NPC472899
0.9118	High Similarity	NPC472898
0.9118	High Similarity	NPC472900
0.9118	High Similarity	NPC309448
0.9109	High Similarity	NPC213190
0.9057	High Similarity	NPC144068
0.9057	High Similarity	NPC51154
0.9048	High Similarity	NPC472987
0.9048	High Similarity	NPC473021
0.9048	High Similarity	NPC476547
0.9038	High Similarity	NPC40440
0.9038	High Similarity	NPC43976
0.9038	High Similarity	NPC248746
0.9038	High Similarity	NPC84956
0.9038	High Similarity	NPC218571
0.9038	High Similarity	NPC102016
0.9038	High Similarity	NPC73243
0.9038	High Similarity	NPC300557
0.9038	High Similarity	NPC194207
0.9038	High Similarity	NPC476835
0.9038	High Similarity	NPC51925
0.9038	High Similarity	NPC474573
0.9038	High Similarity	NPC244086
0.9038	High Similarity	NPC171073
0.9038	High Similarity	NPC154085
0.9038	High Similarity	NPC208383
0.9038	High Similarity	NPC309278
0.9038	High Similarity	NPC470433
0.9038	High Similarity	NPC249265
0.9038	High Similarity	NPC150372
0.9038	High Similarity	NPC475333
0.9038	High Similarity	NPC477809
0.9038	High Similarity	NPC296761
0.9038	High Similarity	NPC302057
0.9038	High Similarity	NPC46190
0.9038	High Similarity	NPC232054
0.9038	High Similarity	NPC6806
0.9038	High Similarity	NPC42482
0.9038	High Similarity	NPC475550
0.9038	High Similarity	NPC22779
0.9038	High Similarity	NPC125361
0.9038	High Similarity	NPC95051
0.9038	High Similarity	NPC224098
0.902	High Similarity	NPC75608
0.9	High Similarity	NPC91497
0.899	High Similarity	NPC243728
0.899	High Similarity	NPC473890
0.8972	High Similarity	NPC477810
0.8972	High Similarity	NPC11548
0.8962	High Similarity	NPC31896
0.8962	High Similarity	NPC210569
0.8962	High Similarity	NPC244431
0.8962	High Similarity	NPC263359
0.8962	High Similarity	NPC32361
0.8952	High Similarity	NPC222202
0.8952	High Similarity	NPC269297
0.8952	High Similarity	NPC224314
0.8952	High Similarity	NPC87998
0.8952	High Similarity	NPC141433
0.8952	High Similarity	NPC23808
0.8952	High Similarity	NPC472717
0.8952	High Similarity	NPC247037
0.8952	High Similarity	NPC477811
0.8942	High Similarity	NPC235824
0.8942	High Similarity	NPC128123
0.8932	High Similarity	NPC26798
0.8932	High Similarity	NPC473199
0.8911	High Similarity	NPC117714
0.8911	High Similarity	NPC31346
0.8911	High Similarity	NPC263756
0.89	High Similarity	NPC158088
0.8899	High Similarity	NPC476692
0.8899	High Similarity	NPC476691
0.8889	High Similarity	NPC148965
0.8889	High Similarity	NPC477029
0.8889	High Similarity	NPC63609
0.8889	High Similarity	NPC477030
0.8889	High Similarity	NPC472989
0.8879	High Similarity	NPC79900
0.8879	High Similarity	NPC476546
0.8879	High Similarity	NPC307642
0.8868	High Similarity	NPC477028
0.8868	High Similarity	NPC477032
0.8868	High Similarity	NPC13193
0.8868	High Similarity	NPC470748
0.8868	High Similarity	NPC472715
0.8868	High Similarity	NPC124677
0.8868	High Similarity	NPC65167
0.8857	High Similarity	NPC250089
0.8857	High Similarity	NPC14630
0.8857	High Similarity	NPC157530
0.8857	High Similarity	NPC472901
0.8835	High Similarity	NPC109792
0.8835	High Similarity	NPC54521
0.8835	High Similarity	NPC57065
0.8835	High Similarity	NPC93352
0.8824	High Similarity	NPC30289
0.8824	High Similarity	NPC256133

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 NPC473469 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	2215
0.2-0.3	4278
0.3-0.4	1605
0.4-0.5	436
0.5-0.6	238
0.6-0.7	125
0.7-0.8	14
0.8-0.85	5
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8661	High Similarity	NPD8033	Approved
0.8661	High Similarity	NPD8380	Approved
0.8661	High Similarity	NPD8379	Approved
0.8661	High Similarity	NPD8378	Approved
0.8661	High Similarity	NPD8296	Approved
0.8661	High Similarity	NPD8335	Approved
0.8571	High Similarity	NPD8294	Approved
0.8571	High Similarity	NPD8377	Approved
0.8393	Intermediate Similarity	NPD7328	Approved
0.8393	Intermediate Similarity	NPD7327	Approved
0.8319	Intermediate Similarity	NPD7516	Approved
0.8218	Intermediate Similarity	NPD8171	Discontinued
0.7982	Intermediate Similarity	NPD6412	Phase 2
0.7876	Intermediate Similarity	NPD8133	Approved
0.7863	Intermediate Similarity	NPD7503	Approved
0.775	Intermediate Similarity	NPD7507	Approved
0.7705	Intermediate Similarity	NPD7319	Approved
0.7522	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD8449	Approved
0.7477	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD8450	Suspended
0.7438	Intermediate Similarity	NPD8328	Phase 3
0.7374	Intermediate Similarity	NPD7525	Registered
0.7339	Intermediate Similarity	NPD7736	Approved
0.7213	Intermediate Similarity	NPD6370	Approved
0.7212	Intermediate Similarity	NPD7524	Approved
0.72	Intermediate Similarity	NPD6928	Phase 2
0.713	Intermediate Similarity	NPD6686	Approved
0.712	Intermediate Similarity	NPD8293	Discontinued
0.71	Intermediate Similarity	NPD7645	Phase 2
0.7087	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6059	Approved
0.7049	Intermediate Similarity	NPD6054	Approved
0.7027	Intermediate Similarity	NPD7638	Approved
0.699	Remote Similarity	NPD6695	Phase 3
0.697	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7640	Approved
0.6964	Remote Similarity	NPD7639	Approved
0.6891	Remote Similarity	NPD8297	Approved
0.6891	Remote Similarity	NPD6882	Approved
0.6887	Remote Similarity	NPD7750	Discontinued
0.688	Remote Similarity	NPD6067	Discontinued
0.6869	Remote Similarity	NPD7339	Approved
0.6869	Remote Similarity	NPD6942	Approved
0.6855	Remote Similarity	NPD6015	Approved
0.6855	Remote Similarity	NPD6016	Approved
0.6825	Remote Similarity	NPD7492	Approved
0.6812	Remote Similarity	NPD7625	Phase 1
0.6803	Remote Similarity	NPD6009	Approved
0.68	Remote Similarity	NPD5988	Approved
0.6774	Remote Similarity	NPD6319	Approved
0.6772	Remote Similarity	NPD6616	Approved
0.6765	Remote Similarity	NPD6929	Approved
0.6729	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8517	Approved
0.672	Remote Similarity	NPD8516	Approved
0.672	Remote Similarity	NPD8515	Approved
0.672	Remote Similarity	NPD8513	Phase 3
0.6719	Remote Similarity	NPD7078	Approved
0.6699	Remote Similarity	NPD6930	Phase 2
0.6699	Remote Similarity	NPD6931	Approved
0.6694	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6639	Remote Similarity	NPD6372	Approved
0.6639	Remote Similarity	NPD6373	Approved
0.6636	Remote Similarity	NPD8034	Phase 2
0.6636	Remote Similarity	NPD8035	Phase 2
0.6634	Remote Similarity	NPD6933	Approved
0.6577	Remote Similarity	NPD6399	Phase 3
0.6569	Remote Similarity	NPD5776	Phase 2
0.6569	Remote Similarity	NPD6925	Approved
0.6569	Remote Similarity	NPD6932	Approved
0.6555	Remote Similarity	NPD6881	Approved
0.6555	Remote Similarity	NPD6899	Approved
0.6555	Remote Similarity	NPD7320	Approved
0.6538	Remote Similarity	NPD6033	Approved
0.6529	Remote Similarity	NPD6649	Approved
0.6529	Remote Similarity	NPD8130	Phase 1
0.6529	Remote Similarity	NPD6650	Approved
0.6518	Remote Similarity	NPD7748	Approved
0.6505	Remote Similarity	NPD7145	Approved
0.6491	Remote Similarity	NPD4755	Approved
0.6491	Remote Similarity	NPD7902	Approved
0.6486	Remote Similarity	NPD7087	Discontinued
0.6471	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD5697	Approved
0.6466	Remote Similarity	NPD4159	Approved
0.646	Remote Similarity	NPD7991	Discontinued
0.6449	Remote Similarity	NPD4786	Approved
0.6446	Remote Similarity	NPD7102	Approved
0.6446	Remote Similarity	NPD7290	Approved
0.6446	Remote Similarity	NPD4634	Approved
0.6446	Remote Similarity	NPD6883	Approved
0.6442	Remote Similarity	NPD6683	Phase 2
0.6436	Remote Similarity	NPD6924	Approved
0.6436	Remote Similarity	NPD4785	Approved
0.6436	Remote Similarity	NPD6926	Approved
0.6436	Remote Similarity	NPD4784	Approved
0.6429	Remote Similarity	NPD4202	Approved
0.641	Remote Similarity	NPD7632	Discontinued
0.64	Remote Similarity	NPD7115	Discovery
0.64	Remote Similarity	NPD4243	Approved
0.6396	Remote Similarity	NPD3168	Discontinued
0.6393	Remote Similarity	NPD6617	Approved
0.6393	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6847	Approved
0.6393	Remote Similarity	NPD6869	Approved
0.6389	Remote Similarity	NPD6893	Approved
0.6389	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6008	Approved
0.6381	Remote Similarity	NPD7514	Phase 3
0.6381	Remote Similarity	NPD4748	Discontinued
0.6379	Remote Similarity	NPD4700	Approved
0.6379	Remote Similarity	NPD5285	Approved
0.6379	Remote Similarity	NPD4696	Approved
0.6379	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD6012	Approved
0.6364	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD7604	Phase 2
0.6348	Remote Similarity	NPD6083	Phase 2
0.6348	Remote Similarity	NPD6084	Phase 2
0.6339	Remote Similarity	NPD7515	Phase 2
0.6339	Remote Similarity	NPD7637	Suspended
0.6328	Remote Similarity	NPD5983	Phase 2
0.6321	Remote Similarity	NPD6902	Approved
0.6306	Remote Similarity	NPD5328	Approved
0.6293	Remote Similarity	NPD4225	Approved
0.6281	Remote Similarity	NPD6011	Approved
0.6275	Remote Similarity	NPD1810	Approved
0.6275	Remote Similarity	NPD1811	Approved
0.6271	Remote Similarity	NPD5225	Approved
0.6271	Remote Similarity	NPD4633	Approved
0.6271	Remote Similarity	NPD5211	Phase 2
0.6271	Remote Similarity	NPD5224	Approved
0.6271	Remote Similarity	NPD5226	Approved
0.6262	Remote Similarity	NPD3667	Approved
0.626	Remote Similarity	NPD6336	Discontinued
0.626	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4768	Approved
0.6238	Remote Similarity	NPD7152	Approved
0.6238	Remote Similarity	NPD7150	Approved
0.6238	Remote Similarity	NPD7151	Approved
0.623	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7900	Approved
0.6228	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7332	Phase 2
0.6226	Remote Similarity	NPD7509	Discontinued
0.6218	Remote Similarity	NPD5175	Approved
0.6218	Remote Similarity	NPD5174	Approved
0.6216	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6922	Approved
0.62	Remote Similarity	NPD6923	Approved
0.6195	Remote Similarity	NPD6079	Approved
0.6186	Remote Similarity	NPD5223	Approved
0.6186	Remote Similarity	NPD5344	Discontinued
0.6182	Remote Similarity	NPD3618	Phase 1
0.6168	Remote Similarity	NPD6898	Phase 1
0.6167	Remote Similarity	NPD5141	Approved
0.6161	Remote Similarity	NPD4753	Phase 2
0.6161	Remote Similarity	NPD6051	Approved
0.6148	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4729	Approved
0.6148	Remote Similarity	NPD4730	Approved
0.6147	Remote Similarity	NPD3666	Approved
0.6147	Remote Similarity	NPD3665	Phase 1
0.6147	Remote Similarity	NPD3133	Approved
0.6139	Remote Similarity	NPD7144	Approved
0.6139	Remote Similarity	NPD7143	Approved
0.6083	Remote Similarity	NPD4754	Approved
0.6074	Remote Similarity	NPD5956	Approved
0.6063	Remote Similarity	NPD6274	Approved
0.6063	Remote Similarity	NPD6940	Discontinued
0.6058	Remote Similarity	NPD5275	Approved
0.6058	Remote Similarity	NPD4190	Phase 3
0.6048	Remote Similarity	NPD5249	Phase 3
0.6048	Remote Similarity	NPD5247	Approved
0.6048	Remote Similarity	NPD5250	Approved
0.6048	Remote Similarity	NPD5251	Approved
0.6048	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5248	Approved
0.6047	Remote Similarity	NPD7101	Approved
0.6047	Remote Similarity	NPD7100	Approved
0.6036	Remote Similarity	NPD6684	Approved
0.6036	Remote Similarity	NPD5330	Approved
0.6036	Remote Similarity	NPD7334	Approved
0.6036	Remote Similarity	NPD6409	Approved
0.6036	Remote Similarity	NPD7146	Approved
0.6036	Remote Similarity	NPD7521	Approved
0.6034	Remote Similarity	NPD5695	Phase 3
0.6017	Remote Similarity	NPD5696	Approved
0.6017	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8174	Phase 2
0.6016	Remote Similarity	NPD5128	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