NPASS Compound

Structure

NPC206900 OpenBabel07101718312D 45 52 0 0 1 0 0 0 0 0999 V2000 -4.3627 -0.5800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2051 3.1065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3283 5.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7795 -0.8561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7105 3.8990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1369 -0.9582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2887 3.0112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2283 -1.0413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2144 1.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6192 1.3924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2201 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5474 1.8685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9917 -0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1560 0.2886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4577 2.6059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5632 3.5619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3398 3.4200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5308 0.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6135 2.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6416 -0.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6385 -0.1960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0270 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3455 2.4200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2917 1.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2856 -0.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4824 1.9150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4881 0.9150 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6822 1.9333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6910 2.9326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5968 -0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2490 3.7418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4709 3.9150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6077 3.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2136 -0.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6762 1.2244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5788 -0.2165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4402 0.5558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3570 0.4200 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1304 2.1092 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1202 2.0293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4651 4.9150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7829 -0.9381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1306 -0.8605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9560 3.6893 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 38 1 0 0 0 0 2 39 1 0 0 0 0 3 41 1 0 0 0 0 4 42 1 0 0 0 0 5 7 2 0 0 0 0 5 22 1 0 0 0 0 6 8 2 0 0 0 0 6 21 1 0 0 0 0 7 29 1 0 0 0 0 8 30 1 0 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 38 1 0 0 0 0 12 39 1 0 0 0 0 13 21 2 0 0 0 0 13 25 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 22 2 0 0 0 0 16 31 1 0 0 0 0 17 23 2 0 0 0 0 17 32 1 0 0 0 0 18 24 2 0 0 0 0 18 34 1 0 0 0 0 19 26 2 0 0 0 0 19 33 1 0 0 0 0 20 25 1 0 0 0 0 20 43 1 0 0 0 0 23 26 1 0 0 0 0 24 35 1 0 0 0 0 25 30 2 0 0 0 0 26 27 1 0 0 0 0 27 14 1 1 0 0 0 27 38 1 0 0 0 0 28 15 1 1 0 0 0 28 35 1 0 0 0 0 28 39 1 0 0 0 0 29 31 2 0 0 0 0 29 40 1 0 0 0 0 30 45 1 0 0 0 0 31 44 1 0 0 0 0 32 33 2 0 0 0 0 32 41 1 0 0 0 0 33 44 1 0 0 0 0 34 36 2 0 0 0 0 34 42 1 0 0 0 0 35 37 2 0 0 0 0 36 37 1 0 0 0 0 36 43 1 0 0 0 0 37 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	606.27
Volume:	623.154
LogP:	6.125
LogD:	3.751
LogS:	-5.965
# Rotatable Bonds:	2
TPSA:	72.86
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.269
Synthetic Accessibility Score:	5.959
Fsp3:	0.351
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.879
MDCK Permeability:	2.1726456907344982e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.308
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.473
Plasma Protein Binding (PPB):	94.06542205810547%
Volume Distribution (VD):	1.042
Pgp-substrate:	5.689208507537842%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.458
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.954
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.95

ADMET: Excretion

Clearance (CL):	8.512
Half-life (T1/2):	0.337

ADMET: Toxicity

hERG Blockers:	0.916
Human Hepatotoxicity (H-HT):	0.026
Drug-inuced Liver Injury (DILI):	0.263
AMES Toxicity:	0.172
Rat Oral Acute Toxicity:	0.261
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.791
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.432

Download Data

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

Natural Product: NPC206900

Natural Product ID:	NPC206900
*Common Name:**	Racemosidine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CQWDLZVYIHGYLN-VSGBNLITSA-N
Standard InCHI:	InChI=1S/C37H38N2O6/c1-38-11-9-23-17-32(41-3)33-19-26(23)27(38)14-21-6-8-30-25(13-21)20-43-36-34(42-4)18-24-10-12-39(2)28(35(24)37(36)45-30)15-22-5-7-29(40)31(16-22)44-33/h5-8,13,16-19,27-28,40H,9-12,14-15,20H2,1-4H3/t27-,28-/m1/s1
SMILES:	COc1cc2CCN([C@H]3c2cc1Oc1cc(ccc1O)C[C@H]1N(C)CCc2c1c1Oc4ccc(C3)cc4COc1c(c2)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172568
PubChem CID:	46872237
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	roots	n.a.	n.a.	PMID[20593839]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18410	Cyclea racemosa	Species	Menispermaceae	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	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	2800.0	nM	PMID[465863]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	6090.0	nM	PMID[465863]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	6700.0	nM	PMID[465863]

☑ 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 NPC206900 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	379
0.1-0.2	1736
0.2-0.3	8451
0.3-0.4	10050
0.4-0.5	5381
0.5-0.6	8578
0.6-0.7	6638
0.7-0.8	1204
0.8-0.85	136
0.85-0.9	50
0.9-0.95	57
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
0.9708	High Similarity	NPC275680
0.9708	High Similarity	NPC22115
0.9704	High Similarity	NPC185639
0.9704	High Similarity	NPC328155
0.9704	High Similarity	NPC104196
0.9704	High Similarity	NPC290582
0.9704	High Similarity	NPC271013
0.9704	High Similarity	NPC222661
0.9704	High Similarity	NPC311973
0.9704	High Similarity	NPC182052
0.9704	High Similarity	NPC251735
0.9704	High Similarity	NPC279228
0.9704	High Similarity	NPC7715
0.9704	High Similarity	NPC54654
0.9704	High Similarity	NPC49075
0.9704	High Similarity	NPC42663
0.9704	High Similarity	NPC239824
0.9704	High Similarity	NPC90998
0.9704	High Similarity	NPC229373
0.9704	High Similarity	NPC223690
0.9704	High Similarity	NPC217748
0.9704	High Similarity	NPC15414
0.9704	High Similarity	NPC290005
0.9704	High Similarity	NPC181796
0.9704	High Similarity	NPC285931
0.9704	High Similarity	NPC8836
0.9704	High Similarity	NPC258657
0.9647	High Similarity	NPC274716
0.9647	High Similarity	NPC254441
0.9647	High Similarity	NPC167116
0.9645	High Similarity	NPC286119
0.9591	High Similarity	NPC302245
0.9591	High Similarity	NPC95426
0.9591	High Similarity	NPC16357
0.9588	High Similarity	NPC30779
0.9535	High Similarity	NPC65312
0.9535	High Similarity	NPC139783
0.9535	High Similarity	NPC116465
0.9535	High Similarity	NPC212237
0.9429	High Similarity	NPC478093
0.9425	High Similarity	NPC175890
0.9425	High Similarity	NPC11296
0.9425	High Similarity	NPC48490
0.9425	High Similarity	NPC82457
0.9425	High Similarity	NPC274661
0.9375	High Similarity	NPC473589
0.9375	High Similarity	NPC478091
0.9375	High Similarity	NPC478092
0.9375	High Similarity	NPC30182
0.9371	High Similarity	NPC191132
0.9371	High Similarity	NPC60295
0.9318	High Similarity	NPC24260
0.929	High Similarity	NPC115284
0.929	High Similarity	NPC317439
0.929	High Similarity	NPC76682
0.929	High Similarity	NPC276890
0.929	High Similarity	NPC227060
0.929	High Similarity	NPC63646
0.929	High Similarity	NPC10908
0.929	High Similarity	NPC317145
0.929	High Similarity	NPC198498
0.9266	High Similarity	NPC256124
0.9235	High Similarity	NPC129518
0.9235	High Similarity	NPC41376
0.9235	High Similarity	NPC12424
0.9235	High Similarity	NPC251580
0.9172	High Similarity	NPC83198
0.9172	High Similarity	NPC204908
0.9128	High Similarity	NPC293093
0.9056	High Similarity	NPC234318
0.9053	High Similarity	NPC250846
0.9053	High Similarity	NPC268503
0.9053	High Similarity	NPC264850
0.9053	High Similarity	NPC42549
0.9053	High Similarity	NPC13916
0.9053	High Similarity	NPC256012
0.9053	High Similarity	NPC317272
0.9053	High Similarity	NPC240841
0.905	High Similarity	NPC85381
0.9045	High Similarity	NPC41122
0.9045	High Similarity	NPC318805
0.9023	High Similarity	NPC475479
0.9023	High Similarity	NPC243454
0.9012	High Similarity	NPC152680
0.9012	High Similarity	NPC232386
0.9012	High Similarity	NPC190783
0.9011	High Similarity	NPC475654
0.8994	High Similarity	NPC24465
0.8977	High Similarity	NPC302275
0.8971	High Similarity	NPC239584
0.892	High Similarity	NPC299990
0.892	High Similarity	NPC73492
0.8865	High Similarity	NPC254581
0.8771	High Similarity	NPC14507
0.8771	High Similarity	NPC47077
0.8736	High Similarity	NPC239775
0.8736	High Similarity	NPC475215
0.8736	High Similarity	NPC108434
0.8715	High Similarity	NPC249996
0.8678	High Similarity	NPC168753
0.8678	High Similarity	NPC118274
0.8674	High Similarity	NPC281581
0.8652	High Similarity	NPC195538
0.8639	High Similarity	NPC247639
0.8639	High Similarity	NPC25084
0.8626	High Similarity	NPC475597
0.8626	High Similarity	NPC473716
0.8603	High Similarity	NPC476202
0.858	High Similarity	NPC469817
0.858	High Similarity	NPC172765
0.858	High Similarity	NPC39701
0.858	High Similarity	NPC204828
0.858	High Similarity	NPC276588
0.858	High Similarity	NPC2413
0.858	High Similarity	NPC249797
0.858	High Similarity	NPC127674
0.858	High Similarity	NPC110416
0.858	High Similarity	NPC184026
0.858	High Similarity	NPC54379
0.858	High Similarity	NPC189266
0.858	High Similarity	NPC295691
0.858	High Similarity	NPC5238
0.858	High Similarity	NPC207757
0.858	High Similarity	NPC278799
0.858	High Similarity	NPC193949
0.8564	High Similarity	NPC82056
0.8547	High Similarity	NPC60186
0.8492	Intermediate Similarity	NPC32154
0.8492	Intermediate Similarity	NPC474507
0.8488	Intermediate Similarity	NPC271388
0.8488	Intermediate Similarity	NPC205255
0.8488	Intermediate Similarity	NPC235143
0.8488	Intermediate Similarity	NPC119649
0.8488	Intermediate Similarity	NPC230956
0.8462	Intermediate Similarity	NPC38964
0.8457	Intermediate Similarity	NPC474931
0.8457	Intermediate Similarity	NPC145832
0.8457	Intermediate Similarity	NPC158376
0.8457	Intermediate Similarity	NPC306555
0.8457	Intermediate Similarity	NPC117188
0.8457	Intermediate Similarity	NPC81218
0.8457	Intermediate Similarity	NPC205421
0.8457	Intermediate Similarity	NPC12053
0.8448	Intermediate Similarity	NPC13504
0.8448	Intermediate Similarity	NPC306843
0.8448	Intermediate Similarity	NPC253043
0.8448	Intermediate Similarity	NPC136508
0.8448	Intermediate Similarity	NPC196447
0.8448	Intermediate Similarity	NPC78222
0.8448	Intermediate Similarity	NPC96603
0.8448	Intermediate Similarity	NPC212794
0.8448	Intermediate Similarity	NPC477563
0.8444	Intermediate Similarity	NPC230276
0.8444	Intermediate Similarity	NPC257269
0.8439	Intermediate Similarity	NPC79402
0.8439	Intermediate Similarity	NPC80759
0.843	Intermediate Similarity	NPC221864
0.8418	Intermediate Similarity	NPC10871
0.8391	Intermediate Similarity	NPC475393
0.8391	Intermediate Similarity	NPC324144
0.8389	Intermediate Similarity	NPC40496
0.8389	Intermediate Similarity	NPC119068
0.838	Intermediate Similarity	NPC476577
0.838	Intermediate Similarity	NPC173416
0.838	Intermediate Similarity	NPC241704
0.838	Intermediate Similarity	NPC148709
0.8343	Intermediate Similarity	NPC97221
0.8343	Intermediate Similarity	NPC220858
0.8343	Intermediate Similarity	NPC88249
0.8343	Intermediate Similarity	NPC151895
0.8343	Intermediate Similarity	NPC192768
0.8286	Intermediate Similarity	NPC1229
0.8284	Intermediate Similarity	NPC103379
0.8284	Intermediate Similarity	NPC477565
0.8276	Intermediate Similarity	NPC166014
0.8276	Intermediate Similarity	NPC27410
0.8256	Intermediate Similarity	NPC123323
0.8239	Intermediate Similarity	NPC232514
0.8239	Intermediate Similarity	NPC238530
0.8239	Intermediate Similarity	NPC276944
0.8239	Intermediate Similarity	NPC169743
0.8225	Intermediate Similarity	NPC428
0.8225	Intermediate Similarity	NPC24233
0.8225	Intermediate Similarity	NPC147390
0.8225	Intermediate Similarity	NPC476571
0.8225	Intermediate Similarity	NPC135538
0.8225	Intermediate Similarity	NPC246587
0.8192	Intermediate Similarity	NPC223077
0.8192	Intermediate Similarity	NPC56887
0.8192	Intermediate Similarity	NPC124657
0.8192	Intermediate Similarity	NPC193853
0.8172	Intermediate Similarity	NPC82763
0.8167	Intermediate Similarity	NPC66341
0.8167	Intermediate Similarity	NPC477020
0.8167	Intermediate Similarity	NPC192135
0.8166	Intermediate Similarity	NPC476151
0.8166	Intermediate Similarity	NPC321505
0.8166	Intermediate Similarity	NPC106295
0.8166	Intermediate Similarity	NPC16107
0.8166	Intermediate Similarity	NPC476144

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 NPC206900 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	798
0.2-0.3	1192
0.3-0.4	2279
0.4-0.5	2360
0.5-0.6	1541
0.6-0.7	630
0.7-0.8	127
0.8-0.85	4
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9704	High Similarity	NPD8053	Approved
0.9704	High Similarity	NPD8054	Approved
0.9349	High Similarity	NPD8156	Discontinued
0.929	High Similarity	NPD8099	Discontinued
0.929	High Similarity	NPD8251	Approved
0.929	High Similarity	NPD8252	Approved
0.8389	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8351	Intermediate Similarity	NPD8095	Phase 1
0.8166	Intermediate Similarity	NPD4584	Approved
0.8162	Intermediate Similarity	NPD7906	Approved
0.8114	Intermediate Similarity	NPD6788	Approved
0.809	Intermediate Similarity	NPD6071	Discontinued
0.7989	Intermediate Similarity	NPD4772	Phase 2
0.7989	Intermediate Similarity	NPD4773	Phase 2
0.7966	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD7831	Phase 2
0.7966	Intermediate Similarity	NPD7833	Phase 2
0.7946	Intermediate Similarity	NPD7313	Approved
0.7946	Intermediate Similarity	NPD7312	Approved
0.7946	Intermediate Similarity	NPD7310	Approved
0.7946	Intermediate Similarity	NPD7311	Approved
0.7906	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD7309	Approved
0.7901	Intermediate Similarity	NPD27	Approved
0.7901	Intermediate Similarity	NPD2489	Approved
0.7898	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD3051	Approved
0.7853	Intermediate Similarity	NPD2560	Approved
0.7853	Intermediate Similarity	NPD2563	Approved
0.7849	Intermediate Similarity	NPD4578	Approved
0.7849	Intermediate Similarity	NPD4577	Approved
0.7845	Intermediate Similarity	NPD2969	Approved
0.7845	Intermediate Similarity	NPD2970	Approved
0.7819	Intermediate Similarity	NPD4663	Approved
0.7811	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7447	Phase 1
0.774	Intermediate Similarity	NPD7298	Approved
0.767	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD2898	Approved
0.7606	Intermediate Similarity	NPD7549	Discontinued
0.7586	Intermediate Similarity	NPD2420	Approved
0.7586	Intermediate Similarity	NPD2421	Approved
0.7586	Intermediate Similarity	NPD7213	Phase 3
0.7586	Intermediate Similarity	NPD7212	Phase 2
0.7582	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4010	Discontinued
0.7473	Intermediate Similarity	NPD4055	Discovery
0.7471	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6031	Approved
0.7458	Intermediate Similarity	NPD6030	Approved
0.7443	Intermediate Similarity	NPD1424	Approved
0.7437	Intermediate Similarity	NPD2494	Approved
0.7437	Intermediate Similarity	NPD3450	Approved
0.7437	Intermediate Similarity	NPD2493	Approved
0.7437	Intermediate Similarity	NPD3452	Approved
0.743	Intermediate Similarity	NPD4678	Approved
0.743	Intermediate Similarity	NPD4675	Approved
0.7429	Intermediate Similarity	NPD3845	Phase 1
0.7423	Intermediate Similarity	NPD2488	Approved
0.7423	Intermediate Similarity	NPD2490	Approved
0.7419	Intermediate Similarity	NPD4481	Phase 3
0.7414	Intermediate Similarity	NPD6748	Discontinued
0.7389	Intermediate Similarity	NPD6072	Discontinued
0.7371	Intermediate Similarity	NPD5241	Discontinued
0.7351	Intermediate Similarity	NPD6107	Approved
0.7346	Intermediate Similarity	NPD6997	Phase 2
0.7344	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7124	Phase 2
0.7327	Intermediate Similarity	NPD4583	Approved
0.7327	Intermediate Similarity	NPD4582	Approved
0.7321	Intermediate Similarity	NPD8153	Approved
0.7321	Intermediate Similarity	NPD8152	Approved
0.7308	Intermediate Similarity	NPD7047	Phase 3
0.7303	Intermediate Similarity	NPD6090	Discontinued
0.73	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5677	Discontinued
0.7288	Intermediate Similarity	NPD7598	Phase 2
0.7278	Intermediate Similarity	NPD4017	Approved
0.7278	Intermediate Similarity	NPD4005	Discontinued
0.7277	Intermediate Similarity	NPD4004	Approved
0.7277	Intermediate Similarity	NPD4002	Approved
0.7263	Intermediate Similarity	NPD3641	Approved
0.7263	Intermediate Similarity	NPD3639	Approved
0.7263	Intermediate Similarity	NPD3640	Phase 3
0.7258	Intermediate Similarity	NPD7802	Discontinued
0.7236	Intermediate Similarity	NPD2974	Approved
0.7236	Intermediate Similarity	NPD2973	Approved
0.7236	Intermediate Similarity	NPD2975	Approved
0.7235	Intermediate Similarity	NPD4475	Approved
0.7235	Intermediate Similarity	NPD4474	Approved
0.7213	Intermediate Similarity	NPD5773	Approved
0.7213	Intermediate Similarity	NPD5772	Approved
0.7211	Intermediate Similarity	NPD42	Phase 2
0.7211	Intermediate Similarity	NPD6042	Phase 2
0.7189	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2200	Suspended
0.7167	Intermediate Similarity	NPD2122	Discontinued
0.7164	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7827	Phase 1
0.716	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5177	Phase 3
0.7151	Intermediate Similarity	NPD4123	Phase 3
0.7143	Intermediate Similarity	NPD5005	Approved
0.7143	Intermediate Similarity	NPD5006	Approved
0.7135	Intermediate Similarity	NPD6666	Approved
0.7135	Intermediate Similarity	NPD6667	Approved
0.7135	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4580	Approved
0.712	Intermediate Similarity	NPD5312	Approved
0.712	Intermediate Similarity	NPD4873	Discontinued
0.712	Intermediate Similarity	NPD5313	Approved
0.712	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7466	Approved
0.7113	Intermediate Similarity	NPD2968	Approved
0.7113	Intermediate Similarity	NPD2971	Approved
0.7093	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1613	Approved
0.7088	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6853	Approved
0.7077	Intermediate Similarity	NPD6851	Approved
0.7076	Intermediate Similarity	NPD5718	Phase 2
0.7073	Intermediate Similarity	NPD4040	Phase 1
0.7072	Intermediate Similarity	NPD7427	Discontinued
0.7068	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4908	Phase 1
0.7056	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4666	Phase 3
0.7006	Intermediate Similarity	NPD7037	Approved
0.7006	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3124	Discontinued
0.6995	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3692	Discontinued
0.698	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5976	Discontinued
0.6974	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5709	Phase 3
0.6966	Remote Similarity	NPD3060	Approved
0.6966	Remote Similarity	NPD4236	Phase 3
0.6966	Remote Similarity	NPD4237	Approved
0.6966	Remote Similarity	NPD4162	Approved
0.6959	Remote Similarity	NPD6297	Approved
0.6949	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4420	Approved
0.6944	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2977	Approved
0.6935	Remote Similarity	NPD4585	Approved
0.6935	Remote Similarity	NPD2978	Approved
0.6927	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5938	Phase 3
0.6923	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5090	Approved
0.6919	Remote Similarity	NPD3027	Phase 3
0.6919	Remote Similarity	NPD5089	Approved
0.6915	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7479	Phase 2
0.6898	Remote Similarity	NPD7907	Approved
0.6897	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2238	Phase 2
0.6893	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6723	Discontinued
0.6889	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2677	Approved
0.6889	Remote Similarity	NPD5160	Discontinued
0.6884	Remote Similarity	NPD6841	Approved
0.6884	Remote Similarity	NPD6843	Phase 3
0.6884	Remote Similarity	NPD7291	Discontinued
0.6884	Remote Similarity	NPD6842	Approved
0.6879	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6111	Discontinued
0.6875	Remote Similarity	NPD6896	Approved
0.6875	Remote Similarity	NPD6895	Approved
0.6872	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7019	Approved
0.6868	Remote Similarity	NPD7020	Approved
0.6862	Remote Similarity	NPD7773	Phase 2
0.6859	Remote Similarity	NPD4166	Phase 2
0.6854	Remote Similarity	NPD7030	Discontinued
0.685	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2904	Discontinued
0.6842	Remote Similarity	NPD3365	Discontinued
0.6839	Remote Similarity	NPD2674	Phase 3
0.6836	Remote Similarity	NPD1753	Discontinued
0.6833	Remote Similarity	NPD6331	Phase 2
0.6833	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7262	Phase 1

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