NPASS Compound

Structure

NPC57628 OpenBabel07101718322D 47 51 0 0 1 0 0 0 0 0999 V2000 3.9790 2.0038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2265 2.9025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9511 3.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5363 1.0815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4217 0.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4307 0.0579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9359 -3.5148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1050 -2.0192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9359 -2.5544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1042 -3.9950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1873 -2.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3187 -1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1042 -2.0742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2725 -3.5148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4833 -1.6491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6147 -0.4297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8714 -0.9794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4703 -0.6336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6892 0.9232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0213 1.9320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8253 2.1517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2471 2.9467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2725 -2.5544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6970 -0.7128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2725 -0.6336 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1855 1.5428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5751 0.9714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7567 1.3572 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3713 0.3106 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5592 -2.0742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9930 -0.0596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6532 0.7040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4703 0.0579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2725 0.0579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8714 0.4037 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4803 2.7255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7749 2.2948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3293 3.2298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3909 -2.5544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2067 0.8767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9505 0.8896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6046 1.0667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4744 1.2577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4608 2.0104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5592 -1.1138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0753 -0.3426 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 23 2 0 0 0 0 14 23 1 0 0 0 0 15 24 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 19 42 1 0 0 0 0 20 36 2 0 0 0 0 20 42 1 0 0 0 0 21 37 2 0 0 0 0 21 43 1 0 0 0 0 22 38 2 0 0 0 0 22 44 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 34 1 6 0 0 0 25 45 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 26 32 1 1 0 0 0 27 29 1 0 0 0 0 27 43 1 1 0 0 0 28 35 1 1 0 0 0 28 44 1 0 0 0 0 29 34 1 6 0 0 0 29 46 1 0 0 0 0 30 39 2 0 0 0 0 30 45 1 0 0 0 0 31 40 2 0 0 0 0 31 46 1 0 0 0 0 32 47 1 0 0 0 0 33 35 1 6 0 0 0 33 41 1 0 0 0 0 34 35 1 1 0 0 0 35 47 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	652.25
Volume:	647.615
LogP:	3.993
LogD:	2.555
LogS:	-3.762
# Rotatable Bonds:	13
TPSA:	160.96
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	5.8
Fsp3:	0.514
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.327
MDCK Permeability:	5.31662481080275e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.113
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.359
Plasma Protein Binding (PPB):	67.14501190185547%
Volume Distribution (VD):	1.722
Pgp-substrate:	15.412923812866211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.937
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.581
CYP3A4-substrate:	0.382

ADMET: Excretion

Clearance (CL):	5.019
Half-life (T1/2):	0.46

ADMET: Toxicity

hERG Blockers:	0.383
Human Hepatotoxicity (H-HT):	0.71
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.188
Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.302
Carcinogencity:	0.459
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC57628

Natural Product ID:	NPC57628
*Common Name:**	MKTPOWHSEPOJAK-MBERIJSPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MKTPOWHSEPOJAK-MBERIJSPSA-N
Standard InCHI:	InChI=1S/C35H40O12/c1-20(36)42-19-34-25(45-30(39)23-13-9-7-10-14-23)17-18-33(6,41)35(34)28(44-22(3)38)26(32(4,5)47-35)27(43-21(2)37)29(34)46-31(40)24-15-11-8-12-16-24/h7-16,25-29,41H,17-19H2,1-6H3/t25-,26+,27-,28+,29+,33-,34-,35-/m0/s1
SMILES:	CC(=O)OC[C@]12[C@H](CC[C@]([C@@]32OC([C@H]([C@@H]([C@H]1OC(=O)c1ccccc1)OC(=O)C)[C@H]3OC(=O)C)(C)C)(C)O)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508131
PubChem CID:	10556235
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[10579879]
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461656]
NPO18386	Maytenus macrocarpa	Species	Celastraceae	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

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[570925]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[570925]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[570925]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[570925]

☑ 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 NPC57628 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	288
0.1-0.2	1055
0.2-0.3	2232
0.3-0.4	4114
0.4-0.5	8245
0.5-0.6	11718
0.6-0.7	12420
0.7-0.8	2085
0.8-0.85	221
0.85-0.9	150
0.9-0.95	55
0.95-1	114

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188865
1.0	High Similarity	NPC95265
1.0	High Similarity	NPC95810
1.0	High Similarity	NPC163719
1.0	High Similarity	NPC476974
1.0	High Similarity	NPC472569
1.0	High Similarity	NPC11685
1.0	High Similarity	NPC472570
1.0	High Similarity	NPC125106
1.0	High Similarity	NPC70716
1.0	High Similarity	NPC472573
1.0	High Similarity	NPC25768
0.9926	High Similarity	NPC472568
0.9926	High Similarity	NPC171525
0.9926	High Similarity	NPC70403
0.9926	High Similarity	NPC174982
0.9926	High Similarity	NPC472575
0.9926	High Similarity	NPC29704
0.9926	High Similarity	NPC472571
0.9926	High Similarity	NPC472572
0.9926	High Similarity	NPC96903
0.9926	High Similarity	NPC184817
0.9926	High Similarity	NPC470157
0.9926	High Similarity	NPC200471
0.9926	High Similarity	NPC471104
0.9926	High Similarity	NPC473088
0.9926	High Similarity	NPC177940
0.9926	High Similarity	NPC470159
0.9926	High Similarity	NPC158663
0.9926	High Similarity	NPC476973
0.9926	High Similarity	NPC469349
0.9853	High Similarity	NPC241951
0.9853	High Similarity	NPC475759
0.9853	High Similarity	NPC475122
0.9853	High Similarity	NPC470152
0.9783	High Similarity	NPC281717
0.9779	High Similarity	NPC163087
0.9778	High Similarity	NPC16912
0.9712	High Similarity	NPC266265
0.9712	High Similarity	NPC471101
0.9712	High Similarity	NPC301556
0.9712	High Similarity	NPC92293
0.9712	High Similarity	NPC476975
0.9712	High Similarity	NPC270590
0.971	High Similarity	NPC474935
0.9704	High Similarity	NPC476094
0.9704	High Similarity	NPC43241
0.9704	High Similarity	NPC473085
0.9704	High Similarity	NPC473758
0.9704	High Similarity	NPC184747
0.9704	High Similarity	NPC473613
0.9704	High Similarity	NPC171207
0.9704	High Similarity	NPC473112
0.9704	High Similarity	NPC97667
0.9704	High Similarity	NPC473081
0.9704	High Similarity	NPC147880
0.9704	High Similarity	NPC48017
0.9704	High Similarity	NPC473109
0.9704	High Similarity	NPC211137
0.9704	High Similarity	NPC473060
0.9704	High Similarity	NPC4341
0.9704	High Similarity	NPC200592
0.9643	High Similarity	NPC473214
0.9643	High Similarity	NPC470245
0.9638	High Similarity	NPC472556
0.9632	High Similarity	NPC87448
0.9632	High Similarity	NPC41481
0.9632	High Similarity	NPC97947
0.9632	High Similarity	NPC291599
0.9632	High Similarity	NPC27377
0.9632	High Similarity	NPC472576
0.9632	High Similarity	NPC118080
0.963	High Similarity	NPC475652
0.963	High Similarity	NPC214550
0.963	High Similarity	NPC210591
0.9574	High Similarity	NPC470153
0.9571	High Similarity	NPC473215
0.9559	High Similarity	NPC275592
0.9559	High Similarity	NPC90614
0.9559	High Similarity	NPC100913
0.9556	High Similarity	NPC283375
0.9556	High Similarity	NPC183122
0.9493	High Similarity	NPC270498
0.9493	High Similarity	NPC246480
0.9493	High Similarity	NPC475429
0.9493	High Similarity	NPC191082
0.9493	High Similarity	NPC473673
0.9493	High Similarity	NPC177340
0.9493	High Similarity	NPC147217
0.9493	High Similarity	NPC139067
0.9489	High Similarity	NPC224491
0.9424	High Similarity	NPC470231
0.9424	High Similarity	NPC51314
0.9424	High Similarity	NPC67777
0.9407	High Similarity	NPC291638
0.9407	High Similarity	NPC472577
0.9407	High Similarity	NPC17877
0.9407	High Similarity	NPC66761
0.9407	High Similarity	NPC195647
0.9375	High Similarity	NPC282239
0.9371	High Similarity	NPC477905
0.9333	High Similarity	NPC474608
0.931	High Similarity	NPC106895
0.9291	High Similarity	NPC473602
0.9281	High Similarity	NPC34012
0.9275	High Similarity	NPC472547
0.9247	High Similarity	NPC472393
0.9236	High Similarity	NPC472548
0.9231	High Similarity	NPC31829
0.9214	High Similarity	NPC91703
0.9197	High Similarity	NPC472551
0.9197	High Similarity	NPC472545
0.9184	High Similarity	NPC471102
0.9178	High Similarity	NPC217091
0.9167	High Similarity	NPC51602
0.9155	High Similarity	NPC209592
0.9155	High Similarity	NPC48599
0.9143	High Similarity	NPC472546
0.913	High Similarity	NPC39549
0.911	High Similarity	NPC472549
0.911	High Similarity	NPC26033
0.911	High Similarity	NPC34066
0.911	High Similarity	NPC228204
0.9097	High Similarity	NPC7095
0.9097	High Similarity	NPC469448
0.9097	High Similarity	NPC112216
0.9097	High Similarity	NPC254558
0.9091	High Similarity	NPC473760
0.9071	High Similarity	NPC266374
0.9041	High Similarity	NPC472030
0.9041	High Similarity	NPC265395
0.9041	High Similarity	NPC472005
0.9041	High Similarity	NPC77719
0.9041	High Similarity	NPC257213
0.9041	High Similarity	NPC256142
0.9041	High Similarity	NPC242262
0.9041	High Similarity	NPC237549
0.9041	High Similarity	NPC249471
0.9041	High Similarity	NPC304876
0.9041	High Similarity	NPC472022
0.9041	High Similarity	NPC1173
0.9041	High Similarity	NPC158333
0.9041	High Similarity	NPC473414
0.9037	High Similarity	NPC147561
0.9034	High Similarity	NPC471103
0.9028	High Similarity	NPC250046
0.9028	High Similarity	NPC60509
0.9028	High Similarity	NPC81698
0.9021	High Similarity	NPC240115
0.9014	High Similarity	NPC38696
0.9014	High Similarity	NPC34943
0.9	High Similarity	NPC183270
0.9	High Similarity	NPC477904
0.898	High Similarity	NPC114410
0.898	High Similarity	NPC473611
0.898	High Similarity	NPC469422
0.898	High Similarity	NPC112523
0.8966	High Similarity	NPC165260
0.8966	High Similarity	NPC161239
0.8966	High Similarity	NPC198455
0.8951	High Similarity	NPC127857
0.8944	High Similarity	NPC477894
0.8933	High Similarity	NPC476077
0.8926	High Similarity	NPC469399
0.8919	High Similarity	NPC326235
0.8919	High Similarity	NPC323001
0.8913	High Similarity	NPC48929
0.8912	High Similarity	NPC472657
0.8912	High Similarity	NPC472658
0.8897	High Similarity	NPC76103
0.8889	High Similarity	NPC20255
0.8873	High Similarity	NPC192658
0.8867	High Similarity	NPC477623
0.8859	High Similarity	NPC318447
0.8859	High Similarity	NPC322048
0.8859	High Similarity	NPC469771
0.8857	High Similarity	NPC475373
0.8851	High Similarity	NPC21410
0.8851	High Similarity	NPC473632
0.8851	High Similarity	NPC469730
0.8851	High Similarity	NPC473670
0.8851	High Similarity	NPC132599
0.8828	High Similarity	NPC217918
0.8824	High Similarity	NPC30171
0.8819	High Similarity	NPC92867
0.8819	High Similarity	NPC311825
0.8819	High Similarity	NPC125882
0.8819	High Similarity	NPC471100
0.8819	High Similarity	NPC471107
0.8815	High Similarity	NPC470753
0.8815	High Similarity	NPC473220
0.8786	High Similarity	NPC472372
0.8786	High Similarity	NPC472374
0.8776	High Similarity	NPC306799
0.8776	High Similarity	NPC101043
0.8776	High Similarity	NPC96308
0.8776	High Similarity	NPC469415
0.8759	High Similarity	NPC478263
0.8759	High Similarity	NPC312393
0.875	High Similarity	NPC253738

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 NPC57628 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	678
0.2-0.3	1350
0.3-0.4	2652
0.4-0.5	2442
0.5-0.6	1299
0.6-0.7	435
0.7-0.8	48
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8099	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD7236	Approved
0.7975	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD7239	Suspended
0.7914	Intermediate Similarity	NPD7799	Discontinued
0.7811	Intermediate Similarity	NPD8434	Phase 2
0.7798	Intermediate Similarity	NPD8407	Phase 2
0.7725	Intermediate Similarity	NPD8368	Discontinued
0.7724	Intermediate Similarity	NPD7008	Discontinued
0.7719	Intermediate Similarity	NPD8360	Approved
0.7719	Intermediate Similarity	NPD8361	Approved
0.7719	Intermediate Similarity	NPD8435	Approved
0.7647	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD8127	Discontinued
0.7602	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8166	Discontinued
0.7557	Intermediate Similarity	NPD8485	Approved
0.75	Intermediate Similarity	NPD7961	Discontinued
0.7469	Intermediate Similarity	NPD7058	Phase 2
0.7469	Intermediate Similarity	NPD7057	Phase 3
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7452	Intermediate Similarity	NPD6273	Approved
0.7432	Intermediate Similarity	NPD3764	Approved
0.743	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4198	Discontinued
0.7399	Intermediate Similarity	NPD8150	Discontinued
0.7397	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD7741	Discontinued
0.7338	Intermediate Similarity	NPD5951	Approved
0.7338	Intermediate Similarity	NPD2629	Approved
0.7337	Intermediate Similarity	NPD5844	Phase 1
0.7333	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7458	Discontinued
0.7308	Intermediate Similarity	NPD6190	Approved
0.7299	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD5125	Phase 3
0.7273	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5126	Approved
0.7273	Intermediate Similarity	NPD6234	Discontinued
0.7256	Intermediate Similarity	NPD4965	Approved
0.7256	Intermediate Similarity	NPD4966	Approved
0.7256	Intermediate Similarity	NPD4967	Phase 2
0.7256	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7003	Approved
0.7239	Intermediate Similarity	NPD7819	Suspended
0.7225	Intermediate Similarity	NPD8312	Approved
0.7225	Intermediate Similarity	NPD8313	Approved
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7228	Approved
0.7153	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7768	Phase 2
0.7134	Intermediate Similarity	NPD8455	Phase 2
0.7134	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7497	Discontinued
0.7118	Intermediate Similarity	NPD7473	Discontinued
0.7108	Intermediate Similarity	NPD7075	Discontinued
0.7103	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7610	Discontinued
0.7055	Intermediate Similarity	NPD4380	Phase 2
0.7055	Intermediate Similarity	NPD6599	Discontinued
0.7041	Intermediate Similarity	NPD6232	Discontinued
0.7034	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2182	Approved
0.7025	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5494	Approved
0.7011	Intermediate Similarity	NPD7685	Pre-registration
0.7011	Intermediate Similarity	NPD7240	Approved
0.6994	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5402	Approved
0.6987	Remote Similarity	NPD5406	Approved
0.6987	Remote Similarity	NPD5404	Approved
0.6987	Remote Similarity	NPD5405	Approved
0.6987	Remote Similarity	NPD5408	Approved
0.6981	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6858	Approved
0.695	Remote Similarity	NPD7094	Approved
0.6948	Remote Similarity	NPD6355	Discontinued
0.6943	Remote Similarity	NPD7266	Discontinued
0.694	Remote Similarity	NPD7699	Phase 2
0.694	Remote Similarity	NPD7700	Phase 2
0.6939	Remote Similarity	NPD6287	Discontinued
0.6928	Remote Similarity	NPD5761	Phase 2
0.6928	Remote Similarity	NPD6663	Approved
0.6928	Remote Similarity	NPD5760	Phase 2
0.6918	Remote Similarity	NPD3750	Approved
0.6914	Remote Similarity	NPD6559	Discontinued
0.6911	Remote Similarity	NPD8462	Phase 1
0.6909	Remote Similarity	NPD7411	Suspended
0.6898	Remote Similarity	NPD8320	Phase 1
0.6898	Remote Similarity	NPD8319	Approved
0.6894	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3226	Approved
0.6887	Remote Similarity	NPD5736	Approved
0.6886	Remote Similarity	NPD3817	Phase 2
0.6882	Remote Similarity	NPD7199	Phase 2
0.6879	Remote Similarity	NPD2935	Discontinued
0.6871	Remote Similarity	NPD5403	Approved
0.6868	Remote Similarity	NPD6534	Approved
0.6868	Remote Similarity	NPD6535	Approved
0.6867	Remote Similarity	NPD6801	Discontinued
0.686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7097	Phase 1
0.6853	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2533	Approved
0.6852	Remote Similarity	NPD5401	Approved
0.6852	Remote Similarity	NPD2532	Approved
0.6852	Remote Similarity	NPD2534	Approved
0.6845	Remote Similarity	NPD7435	Discontinued
0.6839	Remote Similarity	NPD230	Phase 1
0.6835	Remote Similarity	NPD2346	Discontinued
0.6835	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6233	Phase 2
0.6818	Remote Similarity	NPD6765	Approved
0.6818	Remote Similarity	NPD7713	Phase 3
0.6818	Remote Similarity	NPD7714	Approved
0.6818	Remote Similarity	NPD7715	Approved
0.6818	Remote Similarity	NPD6764	Approved
0.6815	Remote Similarity	NPD3748	Approved
0.6815	Remote Similarity	NPD1238	Approved
0.6809	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7095	Approved
0.679	Remote Similarity	NPD6799	Approved
0.6788	Remote Similarity	NPD1929	Approved
0.6788	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1930	Approved
0.6784	Remote Similarity	NPD6959	Discontinued
0.6782	Remote Similarity	NPD3818	Discontinued
0.6772	Remote Similarity	NPD2438	Suspended
0.6769	Remote Similarity	NPD8404	Phase 2
0.6766	Remote Similarity	NPD1934	Approved
0.6763	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6166	Phase 2
0.6763	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6798	Discontinued
0.6748	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD164	Approved
0.6726	Remote Similarity	NPD1465	Phase 2
0.6719	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7874	Approved
0.671	Remote Similarity	NPD8032	Phase 2
0.6709	Remote Similarity	NPD2799	Discontinued
0.6708	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4110	Phase 3
0.6707	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3749	Approved
0.6705	Remote Similarity	NPD7074	Phase 3
0.6702	Remote Similarity	NPD6823	Phase 2
0.6691	Remote Similarity	NPD7798	Approved
0.6684	Remote Similarity	NPD6781	Approved
0.6684	Remote Similarity	NPD6780	Approved
0.6684	Remote Similarity	NPD6777	Approved
0.6684	Remote Similarity	NPD6778	Approved
0.6684	Remote Similarity	NPD6782	Approved
0.6684	Remote Similarity	NPD6776	Approved
0.6684	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6784	Approved
0.6667	Remote Similarity	NPD9545	Approved
0.6648	Remote Similarity	NPD7054	Approved
0.6647	Remote Similarity	NPD3787	Discontinued
0.6647	Remote Similarity	NPD7229	Phase 3
0.6647	Remote Similarity	NPD3882	Suspended
0.6647	Remote Similarity	NPD7028	Phase 2
0.6645	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2313	Discontinued
0.6632	Remote Similarity	NPD7870	Phase 2
0.6632	Remote Similarity	NPD7871	Phase 2
0.6627	Remote Similarity	NPD2801	Approved
0.6625	Remote Similarity	NPD6002	Phase 3
0.6625	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD6005	Phase 3
0.6625	Remote Similarity	NPD5762	Approved
0.6625	Remote Similarity	NPD5763	Approved
0.6625	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD6004	Phase 3
0.6623	Remote Similarity	NPD6832	Phase 2
0.662	Remote Similarity	NPD2067	Discontinued
0.6619	Remote Similarity	NPD5909	Discontinued
0.6615	Remote Similarity	NPD7701	Phase 2

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