NPASS Compound

Structure

NPC234160 OpenBabel07101719512D 57 62 0 0 1 0 0 0 0 0999 V2000 -4.1782 -0.2348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4450 -1.3753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5816 -2.9555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5228 -3.9365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9012 2.8205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9171 2.8205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 -0.4921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8523 1.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4003 0.8990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8612 -1.6975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8238 -1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2027 -2.4288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5144 -0.4921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 1.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2614 0.4921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4091 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9360 0.3041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8523 1.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 -0.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5228 1.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8182 -2.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4823 -1.1707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2401 -2.2242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5228 -2.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9360 -1.2882 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8523 -1.4762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6705 1.4762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9660 -2.4603 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5568 1.4762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7046 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2614 1.4762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6705 0.4921 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1137 -2.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2614 -2.4603 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8182 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2614 -1.4762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9660 0.4921 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1137 -0.9841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9660 1.4762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4091 1.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 0.4921 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8523 0.4921 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3751 1.4762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3751 -2.4603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8523 -2.4603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5228 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1137 -3.9365 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4091 -2.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8182 -0.9841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4091 -0.9841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6705 -2.4603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8182 1.9683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9660 -1.4762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1137 1.9683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1137 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 41 1 0 0 0 0 6 41 1 0 0 0 0 8 43 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 22 2 0 0 0 0 12 23 2 0 0 0 0 13 17 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 31 1 0 0 0 0 16 42 1 0 0 0 0 17 44 1 0 0 0 0 18 43 1 0 0 0 0 19 26 1 0 0 0 0 19 30 1 0 0 0 0 20 45 1 0 0 0 0 21 53 1 0 0 0 0 24 46 2 0 0 0 0 24 53 1 0 0 0 0 25 23 1 1 0 0 0 25 32 1 0 0 0 0 26 32 1 0 0 0 0 26 47 1 1 0 0 0 27 20 1 6 0 0 0 27 33 1 0 0 0 0 27 54 1 0 0 0 0 28 21 1 6 0 0 0 28 34 1 0 0 0 0 28 55 1 0 0 0 0 29 41 1 0 0 0 0 29 42 1 1 0 0 0 30 42 1 1 0 0 0 30 43 1 0 0 0 0 31 41 1 0 0 0 0 31 56 1 1 0 0 0 32 44 1 6 0 0 0 33 36 1 0 0 0 0 33 48 1 1 0 0 0 34 35 1 0 0 0 0 34 49 1 1 0 0 0 35 37 1 0 0 0 0 35 50 1 6 0 0 0 36 38 1 0 0 0 0 36 51 1 6 0 0 0 37 39 1 0 0 0 0 37 52 1 1 0 0 0 38 40 1 0 0 0 0 38 57 1 1 0 0 0 39 55 1 0 0 0 0 39 57 1 6 0 0 0 40 54 1 0 0 0 0 40 56 1 6 0 0 0 42 7 1 1 0 0 0 43 44 1 6 0 0 0 44 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	808.5
Volume:	824.605
LogP:	4.153
LogD:	4.32
LogS:	-3.968
# Rotatable Bonds:	11
TPSA:	204.83
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.096
Synthetic Accessibility Score:	5.902
Fsp3:	0.886
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:	-5.376
MDCK Permeability:	4.838539825868793e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.518
Human Intestinal Absorption (HIA):	0.893
20% Bioavailability (F20%):	0.853
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	94.16944885253906%
Volume Distribution (VD):	0.703
Pgp-substrate:	6.6444926261901855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.396
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	0.94
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.218
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.079
Skin Sensitization:	0.589
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.763

Download Data

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

Natural Product: NPC234160

Natural Product ID:	NPC234160
*Common Name:**	QNOJYUZTGHGWKF-XGZDQIIWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QNOJYUZTGHGWKF-XGZDQIIWSA-N
Standard InCHI:	InChI=1S/C44H72O13/c1-22(2)11-10-12-23(3)25-13-17-44(9)32(25)26(47)19-30-42(7)16-15-31(41(5,6)29(42)14-18-43(30,44)8)56-40-38(36(51)33(48)27(20-45)54-40)57-39-37(52)35(50)34(49)28(55-39)21-53-24(4)46/h11-12,25-40,45,47-52H,10,13-21H2,1-9H3/b23-12-/t25-,26-,27-,28-,29+,30-,31+,32+,33-,34-,35+,36+,37-,38-,39+,40+,42+,43-,44-/m1/s1
SMILES:	CC(=CC/C=C(/C)[C@H]1CC[C@]2(C)[C@@H]1[C@@H](C[C@@H]1[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@@]21C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)C)O1)O)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3600663
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO33292	red ginseng	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26087936]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	Activity	=	95.0	%	PMID[515253]

☑ 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 NPC234160 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	234
0.1-0.2	1778
0.2-0.3	5829
0.3-0.4	13400
0.4-0.5	8863
0.5-0.6	5437
0.6-0.7	3910
0.7-0.8	1810
0.8-0.85	619
0.85-0.9	670
0.9-0.95	118
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
0.9899	High Similarity	NPC472988
0.9899	High Similarity	NPC38217
0.98	High Similarity	NPC125361
0.98	High Similarity	NPC296761
0.98	High Similarity	NPC154085
0.98	High Similarity	NPC51925
0.98	High Similarity	NPC43976
0.9697	High Similarity	NPC473199
0.9608	High Similarity	NPC65167
0.9608	High Similarity	NPC114188
0.9592	High Similarity	NPC312553
0.9592	High Similarity	NPC159036
0.9592	High Similarity	NPC288694
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
0.94	High Similarity	NPC165033
0.94	High Similarity	NPC173583
0.94	High Similarity	NPC273879
0.9388	High Similarity	NPC7341
0.9388	High Similarity	NPC473200
0.9314	High Similarity	NPC295980
0.9307	High Similarity	NPC127801
0.9307	High Similarity	NPC152584
0.9307	High Similarity	NPC160816
0.9307	High Similarity	NPC208477
0.9307	High Similarity	NPC194842
0.9307	High Similarity	NPC269627
0.9307	High Similarity	NPC69737
0.9307	High Similarity	NPC208594
0.9293	High Similarity	NPC129372
0.9293	High Similarity	NPC88000
0.9293	High Similarity	NPC47566
0.9293	High Similarity	NPC472023
0.9293	High Similarity	NPC160734
0.9293	High Similarity	NPC4831
0.9293	High Similarity	NPC309425
0.9286	High Similarity	NPC234287
0.9286	High Similarity	NPC280825
0.9238	High Similarity	NPC144068
0.9216	High Similarity	NPC473469
0.9216	High Similarity	NPC63368
0.9216	High Similarity	NPC231340
0.9216	High Similarity	NPC181467
0.9216	High Similarity	NPC14946
0.9216	High Similarity	NPC208650
0.9208	High Similarity	NPC470885
0.9208	High Similarity	NPC187400
0.9208	High Similarity	NPC221562
0.92	High Similarity	NPC136816
0.9126	High Similarity	NPC159005
0.9126	High Similarity	NPC246124
0.9126	High Similarity	NPC7213
0.9126	High Similarity	NPC180183
0.9126	High Similarity	NPC220427
0.9126	High Similarity	NPC6931
0.9118	High Similarity	NPC242748
0.9109	High Similarity	NPC213190
0.9109	High Similarity	NPC473198
0.9091	High Similarity	NPC157739
0.9065	High Similarity	NPC146652
0.9057	High Similarity	NPC251309
0.9048	High Similarity	NPC250481
0.9048	High Similarity	NPC285410
0.9048	High Similarity	NPC470748
0.9048	High Similarity	NPC263827
0.9038	High Similarity	NPC473844
0.9038	High Similarity	NPC51947
0.9029	High Similarity	NPC190395
0.902	High Similarity	NPC31430
0.902	High Similarity	NPC85593
0.901	High Similarity	NPC154452
0.901	High Similarity	NPC272015
0.901	High Similarity	NPC470053
0.9	High Similarity	NPC282669
0.9	High Similarity	NPC317019
0.8991	High Similarity	NPC55532
0.8991	High Similarity	NPC236973
0.8991	High Similarity	NPC32177
0.8991	High Similarity	NPC470897
0.8991	High Similarity	NPC292467
0.8991	High Similarity	NPC469756
0.8991	High Similarity	NPC30483
0.899	High Similarity	NPC278939
0.899	High Similarity	NPC471770
0.899	High Similarity	NPC473555
0.8972	High Similarity	NPC473882
0.8962	High Similarity	NPC233003
0.8952	High Similarity	NPC129340
0.8952	High Similarity	NPC269095
0.8952	High Similarity	NPC475296
0.8952	High Similarity	NPC78046
0.8952	High Similarity	NPC56713
0.8952	High Similarity	NPC279554
0.8952	High Similarity	NPC29069
0.8952	High Similarity	NPC164194
0.8952	High Similarity	NPC174679
0.8952	High Similarity	NPC90856
0.8952	High Similarity	NPC59804
0.8952	High Similarity	NPC270667
0.8952	High Similarity	NPC136877
0.8952	High Similarity	NPC127056
0.8952	High Similarity	NPC474589
0.8942	High Similarity	NPC88744
0.8942	High Similarity	NPC472896
0.8942	High Similarity	NPC472897
0.8932	High Similarity	NPC472898
0.8932	High Similarity	NPC472900
0.8932	High Similarity	NPC165405
0.8932	High Similarity	NPC309448
0.8932	High Similarity	NPC472899
0.8932	High Similarity	NPC473923
0.8932	High Similarity	NPC473476
0.8911	High Similarity	NPC470054
0.8911	High Similarity	NPC117714
0.8911	High Similarity	NPC263756
0.8911	High Similarity	NPC21064
0.8911	High Similarity	NPC121072
0.8909	High Similarity	NPC72260
0.8909	High Similarity	NPC135369
0.8909	High Similarity	NPC475629
0.8909	High Similarity	NPC475556
0.89	High Similarity	NPC477928
0.8889	High Similarity	NPC63609
0.8889	High Similarity	NPC212660
0.8889	High Similarity	NPC472989
0.8878	High Similarity	NPC211238
0.8868	High Similarity	NPC204392
0.8868	High Similarity	NPC179434
0.8868	High Similarity	NPC11035
0.8868	High Similarity	NPC473021
0.8868	High Similarity	NPC108748
0.8868	High Similarity	NPC297208
0.8868	High Similarity	NPC240734
0.8868	High Similarity	NPC472987
0.8868	High Similarity	NPC164419
0.8868	High Similarity	NPC30397
0.8868	High Similarity	NPC211798
0.8868	High Similarity	NPC275668
0.8868	High Similarity	NPC473481
0.8868	High Similarity	NPC1876
0.8868	High Similarity	NPC91838
0.8868	High Similarity	NPC235841
0.8857	High Similarity	NPC240125
0.8857	High Similarity	NPC250089
0.8857	High Similarity	NPC91583
0.8857	High Similarity	NPC137917
0.8857	High Similarity	NPC14630
0.8857	High Similarity	NPC237503
0.8857	High Similarity	NPC57362
0.8857	High Similarity	NPC157530
0.8857	High Similarity	NPC265655
0.8857	High Similarity	NPC204407
0.8857	High Similarity	NPC167383
0.8857	High Similarity	NPC306746
0.8857	High Similarity	NPC302057
0.8835	High Similarity	NPC470058
0.8835	High Similarity	NPC75608
0.8835	High Similarity	NPC470057
0.8835	High Similarity	NPC312774
0.8835	High Similarity	NPC470059
0.8835	High Similarity	NPC475365
0.8835	High Similarity	NPC470064
0.8835	High Similarity	NPC470060
0.8835	High Similarity	NPC470062
0.8835	High Similarity	NPC470061
0.8835	High Similarity	NPC470043
0.8835	High Similarity	NPC470768
0.8829	High Similarity	NPC120390
0.8829	High Similarity	NPC475590
0.8829	High Similarity	NPC475219
0.8829	High Similarity	NPC231518
0.8829	High Similarity	NPC314535
0.8829	High Similarity	NPC475419
0.8829	High Similarity	NPC474908
0.8829	High Similarity	NPC173555
0.8829	High Similarity	NPC40749
0.8824	High Similarity	NPC30289
0.8824	High Similarity	NPC256133
0.8824	High Similarity	NPC213674
0.8824	High Similarity	NPC76497
0.8818	High Similarity	NPC329905
0.8807	High Similarity	NPC93883
0.8807	High Similarity	NPC477807
0.88	High Similarity	NPC473890
0.88	High Similarity	NPC243728
0.8796	High Similarity	NPC477808
0.8785	High Similarity	NPC324875

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 NPC234160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1988
0.2-0.3	4231
0.3-0.4	1841
0.4-0.5	438
0.5-0.6	280
0.6-0.7	134
0.7-0.8	24
0.8-0.85	6
0.85-0.9	7
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8909	High Similarity	NPD8294	Approved
0.8909	High Similarity	NPD8377	Approved
0.8829	High Similarity	NPD8335	Approved
0.8829	High Similarity	NPD8033	Approved
0.8829	High Similarity	NPD8380	Approved
0.8829	High Similarity	NPD8296	Approved
0.8829	High Similarity	NPD8379	Approved
0.8829	High Similarity	NPD8378	Approved
0.8559	High Similarity	NPD7328	Approved
0.8559	High Similarity	NPD7327	Approved
0.8482	Intermediate Similarity	NPD7516	Approved
0.8364	Intermediate Similarity	NPD8133	Approved
0.8174	Intermediate Similarity	NPD7503	Approved
0.8165	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8051	Intermediate Similarity	NPD7507	Approved
0.8034	Intermediate Similarity	NPD8328	Phase 3
0.7982	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD6412	Phase 2
0.7864	Intermediate Similarity	NPD8171	Discontinued
0.7851	Intermediate Similarity	NPD7319	Approved
0.7748	Intermediate Similarity	NPD6686	Approved
0.7623	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD7638	Approved
0.7477	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7640	Approved
0.7431	Intermediate Similarity	NPD7639	Approved
0.7398	Intermediate Similarity	NPD8293	Discontinued
0.7374	Intermediate Similarity	NPD7525	Registered
0.7264	Intermediate Similarity	NPD8034	Phase 2
0.7264	Intermediate Similarity	NPD8035	Phase 2
0.7213	Intermediate Similarity	NPD6370	Approved
0.7179	Intermediate Similarity	NPD6882	Approved
0.7179	Intermediate Similarity	NPD8297	Approved
0.7131	Intermediate Similarity	NPD8513	Phase 3
0.7131	Intermediate Similarity	NPD8516	Approved
0.7131	Intermediate Similarity	NPD8515	Approved
0.7131	Intermediate Similarity	NPD8517	Approved
0.713	Intermediate Similarity	NPD7748	Approved
0.7109	Intermediate Similarity	NPD8449	Approved
0.71	Intermediate Similarity	NPD7645	Phase 2
0.7097	Intermediate Similarity	NPD7492	Approved
0.7091	Intermediate Similarity	NPD7902	Approved
0.7083	Intermediate Similarity	NPD6009	Approved
0.7059	Intermediate Similarity	NPD7625	Phase 1
0.7054	Intermediate Similarity	NPD8450	Suspended
0.7049	Intermediate Similarity	NPD6319	Approved
0.7049	Intermediate Similarity	NPD6054	Approved
0.7049	Intermediate Similarity	NPD6059	Approved
0.704	Intermediate Similarity	NPD6616	Approved
0.7037	Intermediate Similarity	NPD6399	Phase 3
0.7019	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7078	Approved
0.6975	Remote Similarity	NPD4632	Approved
0.6957	Remote Similarity	NPD7128	Approved
0.6957	Remote Similarity	NPD6675	Approved
0.6957	Remote Similarity	NPD6402	Approved
0.6957	Remote Similarity	NPD5739	Approved
0.6944	Remote Similarity	NPD7515	Phase 2
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD6373	Approved
0.6887	Remote Similarity	NPD7524	Approved
0.688	Remote Similarity	NPD6067	Discontinued
0.6863	Remote Similarity	NPD6928	Phase 2
0.6855	Remote Similarity	NPD6016	Approved
0.6855	Remote Similarity	NPD6015	Approved
0.6842	Remote Similarity	NPD7632	Discontinued
0.6838	Remote Similarity	NPD6881	Approved
0.6838	Remote Similarity	NPD6899	Approved
0.6838	Remote Similarity	NPD7320	Approved
0.6818	Remote Similarity	NPD7900	Approved
0.6818	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6649	Approved
0.6807	Remote Similarity	NPD6650	Approved
0.6807	Remote Similarity	NPD8130	Phase 1
0.6803	Remote Similarity	NPD7115	Discovery
0.68	Remote Similarity	NPD5988	Approved
0.6762	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5701	Approved
0.6752	Remote Similarity	NPD5697	Approved
0.6726	Remote Similarity	NPD4225	Approved
0.6723	Remote Similarity	NPD7102	Approved
0.6723	Remote Similarity	NPD7290	Approved
0.6723	Remote Similarity	NPD6883	Approved
0.67	Remote Similarity	NPD6942	Approved
0.67	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6013	Approved
0.6639	Remote Similarity	NPD6014	Approved
0.6639	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD6083	Phase 2
0.6637	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD7637	Suspended
0.6614	Remote Similarity	NPD7604	Phase 2
0.6606	Remote Similarity	NPD5328	Approved
0.6604	Remote Similarity	NPD4786	Approved
0.6587	Remote Similarity	NPD5983	Phase 2
0.6585	Remote Similarity	NPD6940	Discontinued
0.6574	Remote Similarity	NPD7750	Discontinued
0.6555	Remote Similarity	NPD6011	Approved
0.6555	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6033	Approved
0.6529	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6008	Approved
0.6514	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6336	Discontinued
0.6509	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3669	Approved
0.6505	Remote Similarity	NPD6115	Approved
0.6505	Remote Similarity	NPD6697	Approved
0.6505	Remote Similarity	NPD6118	Approved
0.6505	Remote Similarity	NPD6114	Approved
0.6491	Remote Similarity	NPD4755	Approved
0.6486	Remote Similarity	NPD6079	Approved
0.6481	Remote Similarity	NPD3618	Phase 1
0.6471	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6933	Approved
0.6466	Remote Similarity	NPD5344	Discontinued
0.6455	Remote Similarity	NPD6051	Approved
0.6446	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4634	Approved
0.6442	Remote Similarity	NPD6929	Approved
0.6435	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4202	Approved
0.6415	Remote Similarity	NPD3667	Approved
0.6408	Remote Similarity	NPD6116	Phase 1
0.6381	Remote Similarity	NPD6930	Phase 2
0.6381	Remote Similarity	NPD6931	Approved
0.6379	Remote Similarity	NPD5285	Approved
0.6379	Remote Similarity	NPD5286	Approved
0.6379	Remote Similarity	NPD4700	Approved
0.6379	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6672	Approved
0.6364	Remote Similarity	NPD5737	Approved
0.6336	Remote Similarity	NPD8074	Phase 3
0.633	Remote Similarity	NPD7521	Approved
0.633	Remote Similarity	NPD7146	Approved
0.633	Remote Similarity	NPD6684	Approved
0.633	Remote Similarity	NPD7334	Approved
0.633	Remote Similarity	NPD5330	Approved
0.633	Remote Similarity	NPD6409	Approved
0.632	Remote Similarity	NPD6274	Approved
0.6316	Remote Similarity	NPD5695	Phase 3
0.6311	Remote Similarity	NPD6117	Approved
0.6299	Remote Similarity	NPD7100	Approved
0.6299	Remote Similarity	NPD7101	Approved
0.6293	Remote Similarity	NPD5696	Approved
0.6288	Remote Similarity	NPD8337	Approved
0.6288	Remote Similarity	NPD8336	Approved
0.6275	Remote Similarity	NPD1811	Approved
0.6275	Remote Similarity	NPD6926	Approved
0.6275	Remote Similarity	NPD6924	Approved
0.6275	Remote Similarity	NPD1810	Approved
0.6273	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5211	Phase 2
0.6271	Remote Similarity	NPD5225	Approved
0.6271	Remote Similarity	NPD4633	Approved
0.6271	Remote Similarity	NPD5226	Approved
0.6271	Remote Similarity	NPD5224	Approved
0.6261	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5222	Approved
0.6261	Remote Similarity	NPD4697	Phase 3
0.6261	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD6925	Approved
0.625	Remote Similarity	NPD5776	Phase 2
0.625	Remote Similarity	NPD46	Approved
0.625	Remote Similarity	NPD6932	Approved
0.625	Remote Similarity	NPD6698	Approved
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD7838	Discovery
0.625	Remote Similarity	NPD4768	Approved
0.622	Remote Similarity	NPD6335	Approved
0.6218	Remote Similarity	NPD5175	Approved
0.6218	Remote Similarity	NPD5174	Approved
0.6216	Remote Similarity	NPD6903	Approved
0.6207	Remote Similarity	NPD5173	Approved
0.6202	Remote Similarity	NPD6908	Approved
0.6202	Remote Similarity	NPD6909	Approved
0.6198	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6411	Approved
0.6195	Remote Similarity	NPD7087	Discontinued
0.619	Remote Similarity	NPD6868	Approved
0.619	Remote Similarity	NPD7145	Approved
0.6186	Remote Similarity	NPD5223	Approved
0.6174	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7991	Discontinued
0.6167	Remote Similarity	NPD5141	Approved
0.6161	Remote Similarity	NPD4753	Phase 2
0.6148	Remote Similarity	NPD4730	Approved
0.6148	Remote Similarity	NPD4729	Approved
0.6147	Remote Similarity	NPD3665	Phase 1
0.6147	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD3666	Approved
0.6147	Remote Similarity	NPD3133	Approved
0.6142	Remote Similarity	NPD6317	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