NPASS Compound

Structure

NPC470176 OpenBabel07101719252D 43 46 0 0 1 0 0 0 0 0999 V2000 -1.0013 4.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8968 3.4921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1390 1.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8801 2.8569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8827 3.5220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9483 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 3.2709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2412 1.6322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8090 2.3198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9142 1.1839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 3.2709 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0000 1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5000 2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0000 1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0878 4.0799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1730 2.1498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5000 2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5000 2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0000 1.7321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.6213 0.4768 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.8660 0.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3190 4.9935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1910 2.3198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4659 2.8569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 24 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 29 1 0 0 0 0 15 28 1 0 0 0 0 16 27 1 0 0 0 0 17 30 1 0 0 0 0 18 30 1 0 0 0 0 18 32 1 0 0 0 0 19 26 1 0 0 0 0 19 31 1 6 0 0 0 20 25 1 1 0 0 0 20 39 1 0 0 0 0 21 27 1 6 0 0 0 21 38 1 0 0 0 0 22 12 1 6 0 0 0 22 29 1 0 0 0 0 22 38 1 0 0 0 0 23 13 1 6 0 0 0 23 28 1 0 0 0 0 23 41 1 0 0 0 0 24 30 1 6 0 0 0 24 40 1 0 0 0 0 25 33 1 0 0 0 0 26 42 1 0 0 0 0 27 5 1 6 0 0 0 27 40 1 0 0 0 0 28 6 1 1 0 0 0 28 39 1 0 0 0 0 29 7 1 6 0 0 0 29 42 1 0 0 0 0 30 34 1 0 0 0 0 35 43 1 0 0 0 0 36 43 2 0 0 0 0 37 43 2 0 0 0 0 41 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	700.25
Volume:	627.695
LogP:	3.311
LogD:	1.715
LogS:	-2.494
# Rotatable Bonds:	10
TPSA:	161.21
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.193
Synthetic Accessibility Score:	5.867
Fsp3:	1.0
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:	-5.278
MDCK Permeability:	8.530397280992474e-06
Pgp-inhibitor:	0.964
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.214
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.811

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	86.43128967285156%
Volume Distribution (VD):	0.74
Pgp-substrate:	8.092970848083496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.892
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.648
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	4.394
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.816
Drug-inuced Liver Injury (DILI):	0.059
AMES Toxicity:	0.38
Rat Oral Acute Toxicity:	0.347
Maximum Recommended Daily Dose:	0.453
Skin Sensitization:	0.93
Carcinogencity:	0.592
Eye Corrosion:	0.007
Eye Irritation:	0.019
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC470176

Natural Product ID:	NPC470176
*Common Name:**	[(1S)-4-[(2R,4As,6R,8Ar)-2-[(2S,5R)-5-Bromo-2,6,6-Trimethyloxan-2-Yl]-4A-Methyl-3,4,6,7,8,8A-Hexahydro-2H-Pyrano[3,2-B]Pyran-6-Yl]-4,5-Dihydroxy-1-[(2R,5R)-5-(2-Hydroxypropan-2-Yl)-2-Methyloxolan-2-Yl]Pentyl] Hydrogen Sulfate
IUPAC Name:	[(1S)-4-[(2R,4aS,6R,8aR)-2-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-4a-methyl-3,4,6,7,8,8a-hexahydro-2H-pyrano[3,2-b]pyran-6-yl]-4,5-dihydroxy-1-[(2R,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]pentyl] hydrogen sulfate
Synonyms:
Standard InCHIKey:	QKFMEKNOKHBFQY-ILSRICCPSA-N
Standard InCHI:	InChI=1S/C30H53BrO11S/c1-25(2,33)20-11-15-28(6,39-20)23(41-43(35,36)37)13-17-30(34,18-32)24-9-8-21-27(5,40-24)16-12-22(38-21)29(7)14-10-19(31)26(3,4)42-29/h19-24,32-34H,8-18H2,1-7H3,(H,35,36,37)/t19-,20-,21-,22-,23+,24-,27+,28-,29+,30?/m1/s1
SMILES:	CC1(C(CCC(O1)(C)C2CCC3(C(O2)CCC(O3)C(CCC(C4(CCC(O4)C(C)(C)O)C)OS(=O)(=O)O)(CO)O)C)Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1806667
PubChem CID:	53375686
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO3322	Laurencia viridis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21616566]

☑ 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	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	6900.0	nM	PMID[459896]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	27500.0	nM	PMID[459896]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13500.0	nM	PMID[459896]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11000.0	nM	PMID[459896]

☑ 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 NPC470176 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	357
0.1-0.2	4631
0.2-0.3	16289
0.3-0.4	10839
0.4-0.5	7219
0.5-0.6	2998
0.6-0.7	349
0.7-0.8	8
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC470174
0.9429	High Similarity	NPC470173
0.9143	High Similarity	NPC253123
0.8553	High Similarity	NPC244002
0.8395	Intermediate Similarity	NPC470175
0.7901	Intermediate Similarity	NPC5361
0.7529	Intermediate Similarity	NPC51267
0.7471	Intermediate Similarity	NPC231784
0.7442	Intermediate Similarity	NPC247826
0.7412	Intermediate Similarity	NPC115995
0.725	Intermediate Similarity	NPC138273
0.6974	Remote Similarity	NPC476702
0.6923	Remote Similarity	NPC477761
0.6923	Remote Similarity	NPC477754
0.6923	Remote Similarity	NPC477760
0.6923	Remote Similarity	NPC477758
0.6923	Remote Similarity	NPC477759
0.6795	Remote Similarity	NPC477756
0.6795	Remote Similarity	NPC477751
0.6795	Remote Similarity	NPC477752
0.6795	Remote Similarity	NPC477764
0.6667	Remote Similarity	NPC279575
0.6627	Remote Similarity	NPC470630
0.6622	Remote Similarity	NPC322148
0.6593	Remote Similarity	NPC51662
0.6579	Remote Similarity	NPC472026
0.6548	Remote Similarity	NPC472950
0.6548	Remote Similarity	NPC472952
0.65	Remote Similarity	NPC179823
0.6444	Remote Similarity	NPC320824
0.6437	Remote Similarity	NPC170595
0.6429	Remote Similarity	NPC166250
0.6395	Remote Similarity	NPC474003
0.6364	Remote Similarity	NPC477755
0.6364	Remote Similarity	NPC477753
0.6364	Remote Similarity	NPC477763
0.6364	Remote Similarity	NPC477750
0.6364	Remote Similarity	NPC477757
0.6364	Remote Similarity	NPC477762
0.6322	Remote Similarity	NPC272841
0.6322	Remote Similarity	NPC177343
0.6322	Remote Similarity	NPC43463
0.631	Remote Similarity	NPC470659
0.631	Remote Similarity	NPC83368
0.631	Remote Similarity	NPC470660
0.6304	Remote Similarity	NPC477389
0.6304	Remote Similarity	NPC477387
0.6289	Remote Similarity	NPC469710
0.6282	Remote Similarity	NPC172622
0.6279	Remote Similarity	NPC293223
0.6279	Remote Similarity	NPC136424
0.6265	Remote Similarity	NPC471879
0.6263	Remote Similarity	NPC473616
0.625	Remote Similarity	NPC477282
0.625	Remote Similarity	NPC470623
0.625	Remote Similarity	NPC81074
0.625	Remote Similarity	NPC224003
0.625	Remote Similarity	NPC323231
0.625	Remote Similarity	NPC171741
0.625	Remote Similarity	NPC18724
0.625	Remote Similarity	NPC250836
0.6237	Remote Similarity	NPC314364
0.6235	Remote Similarity	NPC308489
0.6235	Remote Similarity	NPC470151
0.6222	Remote Similarity	NPC477446
0.6222	Remote Similarity	NPC477447
0.6222	Remote Similarity	NPC470155
0.622	Remote Similarity	NPC67099
0.6207	Remote Similarity	NPC11907
0.6207	Remote Similarity	NPC474574
0.6207	Remote Similarity	NPC188793
0.6207	Remote Similarity	NPC133596
0.6207	Remote Similarity	NPC64081
0.6186	Remote Similarity	NPC148593
0.6186	Remote Similarity	NPC473503
0.6186	Remote Similarity	NPC253611
0.6186	Remote Similarity	NPC77717
0.6186	Remote Similarity	NPC471373
0.6186	Remote Similarity	NPC305418
0.6186	Remote Similarity	NPC267238
0.6184	Remote Similarity	NPC472025
0.6184	Remote Similarity	NPC219040
0.618	Remote Similarity	NPC472943
0.618	Remote Similarity	NPC472951
0.6163	Remote Similarity	NPC150938
0.6163	Remote Similarity	NPC36479
0.6154	Remote Similarity	NPC241959
0.6154	Remote Similarity	NPC475412
0.6146	Remote Similarity	NPC473637
0.6146	Remote Similarity	NPC229801
0.6146	Remote Similarity	NPC307167
0.6146	Remote Similarity	NPC210759
0.6146	Remote Similarity	NPC476668
0.6136	Remote Similarity	NPC191345
0.6136	Remote Similarity	NPC252483
0.6129	Remote Similarity	NPC471410
0.6129	Remote Similarity	NPC471411
0.6129	Remote Similarity	NPC107603
0.6122	Remote Similarity	NPC471424
0.6122	Remote Similarity	NPC189575
0.6122	Remote Similarity	NPC205129
0.6122	Remote Similarity	NPC474399
0.6122	Remote Similarity	NPC106701
0.6122	Remote Similarity	NPC471429
0.6122	Remote Similarity	NPC471425
0.6111	Remote Similarity	NPC211049
0.6111	Remote Similarity	NPC470154
0.6111	Remote Similarity	NPC470156
0.6105	Remote Similarity	NPC82955
0.6105	Remote Similarity	NPC131466
0.6104	Remote Similarity	NPC34877
0.6104	Remote Similarity	NPC290179
0.6104	Remote Similarity	NPC317023
0.61	Remote Similarity	NPC473638
0.6082	Remote Similarity	NPC476669
0.6082	Remote Similarity	NPC141769
0.6082	Remote Similarity	NPC325828
0.6082	Remote Similarity	NPC477547
0.6082	Remote Similarity	NPC249204
0.6082	Remote Similarity	NPC234352
0.6082	Remote Similarity	NPC177834
0.6082	Remote Similarity	NPC250393
0.6082	Remote Similarity	NPC48339
0.6082	Remote Similarity	NPC477451
0.6082	Remote Similarity	NPC297348
0.6071	Remote Similarity	NPC53760
0.6071	Remote Similarity	NPC52268
0.6064	Remote Similarity	NPC140446
0.6064	Remote Similarity	NPC43912
0.6061	Remote Similarity	NPC304011
0.6061	Remote Similarity	NPC139271
0.6061	Remote Similarity	NPC473287
0.6053	Remote Similarity	NPC148424
0.6049	Remote Similarity	NPC471760
0.6049	Remote Similarity	NPC190418
0.6049	Remote Similarity	NPC471761
0.6044	Remote Similarity	NPC475388
0.6026	Remote Similarity	NPC185116
0.6024	Remote Similarity	NPC471472
0.6024	Remote Similarity	NPC473294
0.6023	Remote Similarity	NPC476719
0.6022	Remote Similarity	NPC290612
0.6022	Remote Similarity	NPC469555
0.602	Remote Similarity	NPC217205
0.602	Remote Similarity	NPC131693
0.602	Remote Similarity	NPC179859
0.602	Remote Similarity	NPC294686
0.602	Remote Similarity	NPC291203
0.602	Remote Similarity	NPC475436
0.602	Remote Similarity	NPC45959
0.602	Remote Similarity	NPC475325
0.602	Remote Similarity	NPC174024
0.602	Remote Similarity	NPC252253
0.602	Remote Similarity	NPC291547
0.602	Remote Similarity	NPC471464
0.602	Remote Similarity	NPC264101
0.602	Remote Similarity	NPC253268
0.602	Remote Similarity	NPC473851
0.602	Remote Similarity	NPC312678
0.602	Remote Similarity	NPC222731
0.6	Remote Similarity	NPC319030
0.6	Remote Similarity	NPC186594
0.6	Remote Similarity	NPC131506
0.6	Remote Similarity	NPC157777
0.6	Remote Similarity	NPC16449
0.6	Remote Similarity	NPC274200
0.598	Remote Similarity	NPC477225
0.5978	Remote Similarity	NPC478054
0.5977	Remote Similarity	NPC231680
0.5977	Remote Similarity	NPC91387
0.5977	Remote Similarity	NPC270306
0.596	Remote Similarity	NPC475351
0.596	Remote Similarity	NPC107188
0.596	Remote Similarity	NPC107962
0.596	Remote Similarity	NPC6295
0.596	Remote Similarity	NPC477494
0.596	Remote Similarity	NPC211354
0.596	Remote Similarity	NPC473727
0.596	Remote Similarity	NPC473610
0.596	Remote Similarity	NPC19400
0.596	Remote Similarity	NPC206003
0.5957	Remote Similarity	NPC477283
0.5957	Remote Similarity	NPC215968
0.5957	Remote Similarity	NPC470657
0.5957	Remote Similarity	NPC155531
0.5957	Remote Similarity	NPC268633
0.5952	Remote Similarity	NPC16964
0.5952	Remote Similarity	NPC470833
0.5941	Remote Similarity	NPC471374
0.5941	Remote Similarity	NPC471375
0.5941	Remote Similarity	NPC209798
0.5934	Remote Similarity	NPC118116
0.5934	Remote Similarity	NPC116320
0.5934	Remote Similarity	NPC216941
0.5934	Remote Similarity	NPC119922
0.593	Remote Similarity	NPC123122
0.593	Remote Similarity	NPC169085
0.593	Remote Similarity	NPC225748
0.593	Remote Similarity	NPC476709
0.593	Remote Similarity	NPC39266

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 NPC470176 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	4489
0.2-0.3	3149
0.3-0.4	641
0.4-0.5	399
0.5-0.6	106
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6329	Remote Similarity	NPD371	Approved
0.6082	Remote Similarity	NPD8171	Discontinued
0.6071	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD6123	Approved
0.5862	Remote Similarity	NPD1811	Approved
0.5862	Remote Similarity	NPD1810	Approved
0.5658	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD888	Phase 3
0.5658	Remote Similarity	NPD891	Phase 3
0.5658	Remote Similarity	NPD893	Approved
0.5658	Remote Similarity	NPD889	Approved
0.5658	Remote Similarity	NPD895	Approved
0.5658	Remote Similarity	NPD894	Approved
0.5658	Remote Similarity	NPD887	Approved
0.5658	Remote Similarity	NPD892	Phase 3
0.5641	Remote Similarity	NPD2267	Suspended

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