NPASS Compound

Structure

NPC472283 OpenBabel07101718322D 44 48 0 0 1 0 0 0 0 0999 V2000 -0.2713 -4.2680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5632 -2.3315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1858 3.3300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4896 0.8480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9792 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7370 -0.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0205 0.9115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8629 3.5828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4942 -3.6575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0409 0.2027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6873 -0.2923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8890 -0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6452 -0.0887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3449 -1.7557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0409 -2.7349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4795 -1.6644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3483 -2.6892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5798 2.7195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5850 -1.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1929 -1.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4969 -1.2661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1929 -0.2869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0409 -1.7557 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8890 -3.2245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4777 1.3935 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6236 0.4252 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4969 -0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7370 -1.7557 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0564 -0.7527 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1139 -2.0787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2433 2.0040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8890 -1.2661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3449 0.2027 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4913 3.0772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8890 -4.2037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1991 0.6923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0254 -2.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1548 1.6462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0973 2.9723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1348 -0.9367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4338 1.7512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7370 -2.7349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9679 -1.1104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 8 40 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 33 1 0 0 0 0 13 41 1 0 0 0 0 14 20 2 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 16 19 2 0 0 0 0 16 41 1 0 0 0 0 17 30 1 0 0 0 0 18 35 2 0 0 0 0 18 42 1 0 0 0 0 19 28 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 14 1 1 0 0 0 21 27 1 0 0 0 0 21 29 1 0 0 0 0 22 34 1 6 0 0 0 23 33 1 6 0 0 0 24 36 2 0 0 0 0 24 43 1 0 0 0 0 25 26 1 0 0 0 0 25 31 1 6 0 0 0 25 42 1 0 0 0 0 26 32 1 0 0 0 0 26 34 1 1 0 0 0 27 34 1 0 0 0 0 27 37 2 0 0 0 0 28 33 1 1 0 0 0 28 43 1 0 0 0 0 29 32 1 0 0 0 0 29 44 1 6 0 0 0 30 38 2 0 0 0 0 30 44 1 0 0 0 0 31 39 2 0 0 0 0 31 40 1 0 0 0 0 33 6 1 1 0 0 0 34 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.28
Volume:	618.012
LogP:	4.207
LogD:	3.092
LogS:	-5.086
# Rotatable Bonds:	9
TPSA:	135.41
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.244
Synthetic Accessibility Score:	6.159
Fsp3:	0.618
Lipinski Rule-of-5:	Accepted
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:	-4.919
MDCK Permeability:	3.7894784327363595e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.911
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.691
Plasma Protein Binding (PPB):	81.4950180053711%
Volume Distribution (VD):	2.203
Pgp-substrate:	10.196285247802734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.637
CYP2C19-substrate:	0.122
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.637

ADMET: Excretion

Clearance (CL):	9.119
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.494
Human Hepatotoxicity (H-HT):	0.799
Drug-inuced Liver Injury (DILI):	0.729
AMES Toxicity:	0.444
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.235
Carcinogencity:	0.192
Eye Corrosion:	0.007
Eye Irritation:	0.031
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC472283

Natural Product ID:	NPC472283
*Common Name:**	QYULJHYYKMGSKH-ZPGLWJSISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QYULJHYYKMGSKH-ZPGLWJSISA-N
Standard InCHI:	InChI=1S/C34H42O10/c1-9-17(2)30(38)44-29-21-14-20-22(10-12-33(6)23(20)15-24(36)43-28(33)19-11-13-41-16-19)34(7,27(21)37)26(32(29,4)5)25(31(39)40-8)42-18(3)35/h9,11,13-14,16,21-23,25-26,28-29H,10,12,15H2,1-8H3/b17-9+/t21-,22-,23-,25+,26-,28-,29+,33+,34+/m0/s1
SMILES:	COC(=O)[C@@H]([C@H]1C(C)(C)[C@H](OC(=O)/C(=C/C)/C)[C@@H]2C(=O)[C@]1(C)[C@H]1CC[C@@]3([C@H](C1=C2)CC(=O)O[C@H]3c1ccoc1)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357581
PubChem CID:	14587331
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO3136	Swietenia macrophylla	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579863]
NPO3136	Swietenia macrophylla	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[25330401]
NPO3136	Swietenia macrophylla	Species	Meliaceae	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
EC50	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT194	Organism	Dengue virus 2	Dengue virus 2	EC50	=	6300.0	nM	PMID[478582]
NPT27	Others	Unspecified		CC50	=	83000.0	nM	PMID[478582]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	13.2	n.a.	PMID[478582]

☑ 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 NPC472283 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	420
0.1-0.2	1489
0.2-0.3	3333
0.3-0.4	6063
0.4-0.5	10245
0.5-0.6	9982
0.6-0.7	8768
0.7-0.8	1972
0.8-0.85	244
0.85-0.9	108
0.9-0.95	64
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9603	High Similarity	NPC286722
0.9595	High Similarity	NPC159927
0.9595	High Similarity	NPC469335
0.9545	High Similarity	NPC469849
0.9542	High Similarity	NPC69028
0.9542	High Similarity	NPC470939
0.9539	High Similarity	NPC475295
0.9539	High Similarity	NPC473473
0.9536	High Similarity	NPC209364
0.9536	High Similarity	NPC60973
0.9484	High Similarity	NPC470875
0.9481	High Similarity	NPC292389
0.9481	High Similarity	NPC469338
0.947	High Similarity	NPC469850
0.9463	High Similarity	NPC46551
0.9423	High Similarity	NPC473766
0.9423	High Similarity	NPC473753
0.9419	High Similarity	NPC470940
0.9419	High Similarity	NPC276551
0.9412	High Similarity	NPC477403
0.9412	High Similarity	NPC237155
0.9408	High Similarity	NPC107646
0.9355	High Similarity	NPC477405
0.9351	High Similarity	NPC191828
0.9351	High Similarity	NPC305016
0.9351	High Similarity	NPC475381
0.9351	High Similarity	NPC25255
0.9346	High Similarity	NPC167142
0.9342	High Similarity	NPC469336
0.9333	High Similarity	NPC196864
0.9333	High Similarity	NPC477404
0.9324	High Similarity	NPC262198
0.9299	High Similarity	NPC472282
0.9299	High Similarity	NPC173516
0.9295	High Similarity	NPC476857
0.9295	High Similarity	NPC476858
0.9295	High Similarity	NPC476856
0.929	High Similarity	NPC193798
0.929	High Similarity	NPC5079
0.929	High Similarity	NPC329938
0.9281	High Similarity	NPC263265
0.9281	High Similarity	NPC126723
0.9276	High Similarity	NPC178932
0.9241	High Similarity	NPC160651
0.9241	High Similarity	NPC471397
0.9231	High Similarity	NPC476197
0.9231	High Similarity	NPC234660
0.9231	High Similarity	NPC469846
0.9231	High Similarity	NPC51568
0.9226	High Similarity	NPC472653
0.9226	High Similarity	NPC477402
0.9216	High Similarity	NPC476262
0.9211	High Similarity	NPC476201
0.9177	High Similarity	NPC476853
0.9177	High Similarity	NPC476850
0.9177	High Similarity	NPC476861
0.9172	High Similarity	NPC476860
0.9172	High Similarity	NPC123088
0.9167	High Similarity	NPC263432
0.9167	High Similarity	NPC82851
0.9114	High Similarity	NPC23387
0.9114	High Similarity	NPC475779
0.9108	High Similarity	NPC134254
0.9108	High Similarity	NPC39986
0.9108	High Similarity	NPC302369
0.9103	High Similarity	NPC335761
0.9097	High Similarity	NPC173544
0.9097	High Similarity	NPC249021
0.9091	High Similarity	NPC281258
0.9091	High Similarity	NPC264943
0.9085	High Similarity	NPC469503
0.9079	High Similarity	NPC476122
0.9062	High Similarity	NPC302392
0.906	High Similarity	NPC142113
0.9057	High Similarity	NPC472775
0.9057	High Similarity	NPC472774
0.9045	High Similarity	NPC290400
0.9045	High Similarity	NPC472771
0.9045	High Similarity	NPC96443
0.9038	High Similarity	NPC307383
0.9038	High Similarity	NPC473368
0.9032	High Similarity	NPC469485
0.8987	High Similarity	NPC472773
0.8974	High Similarity	NPC472772
0.8968	High Similarity	NPC44675
0.8968	High Similarity	NPC214541
0.8938	High Similarity	NPC476224
0.8924	High Similarity	NPC197596
0.8924	High Similarity	NPC117986
0.8903	High Similarity	NPC30222
0.8903	High Similarity	NPC282445
0.8896	High Similarity	NPC18135
0.8882	High Similarity	NPC472652
0.8882	High Similarity	NPC327922
0.8882	High Similarity	NPC271235
0.8882	High Similarity	NPC470941
0.8868	High Similarity	NPC224394
0.8868	High Similarity	NPC663
0.8854	High Similarity	NPC36655
0.8854	High Similarity	NPC45101
0.8854	High Similarity	NPC261597
0.8846	High Similarity	NPC35000
0.8834	High Similarity	NPC469848
0.882	High Similarity	NPC472651
0.8812	High Similarity	NPC470182
0.8808	High Similarity	NPC86935
0.8805	High Similarity	NPC200782
0.8805	High Similarity	NPC207978
0.8805	High Similarity	NPC149896
0.8805	High Similarity	NPC6326
0.8805	High Similarity	NPC211777
0.8797	High Similarity	NPC475967
0.8788	High Similarity	NPC478177
0.8784	High Similarity	NPC476943
0.8774	High Similarity	NPC116717
0.8773	High Similarity	NPC160818
0.8773	High Similarity	NPC169299
0.8758	High Similarity	NPC478178
0.8758	High Similarity	NPC221809
0.875	High Similarity	NPC419
0.875	High Similarity	NPC198047
0.8734	High Similarity	NPC469847
0.8734	High Similarity	NPC187149
0.8718	High Similarity	NPC44577
0.8716	High Similarity	NPC310830
0.8712	High Similarity	NPC82602
0.871	High Similarity	NPC156189
0.8704	High Similarity	NPC100333
0.8696	High Similarity	NPC271657
0.8693	High Similarity	NPC471292
0.8688	High Similarity	NPC18347
0.8688	High Similarity	NPC471167
0.8688	High Similarity	NPC471166
0.8679	High Similarity	NPC262872
0.8671	High Similarity	NPC204663
0.8667	High Similarity	NPC94763
0.8667	High Similarity	NPC236004
0.8658	High Similarity	NPC220094
0.8654	High Similarity	NPC272590
0.8645	High Similarity	NPC471001
0.8645	High Similarity	NPC470790
0.8645	High Similarity	NPC329180
0.8645	High Similarity	NPC470791
0.8642	High Similarity	NPC93172
0.8642	High Similarity	NPC97574
0.8625	High Similarity	NPC470789
0.8625	High Similarity	NPC333139
0.8618	High Similarity	NPC223415
0.8616	High Similarity	NPC472778
0.8616	High Similarity	NPC472776
0.8616	High Similarity	NPC195131
0.8616	High Similarity	NPC299038
0.8616	High Similarity	NPC472777
0.8614	High Similarity	NPC167340
0.8608	High Similarity	NPC92979
0.8608	High Similarity	NPC75310
0.8599	High Similarity	NPC75906
0.8589	High Similarity	NPC478179
0.8571	High Similarity	NPC188649
0.8562	High Similarity	NPC474932
0.8562	High Similarity	NPC238843
0.8562	High Similarity	NPC199044
0.8562	High Similarity	NPC474611
0.8562	High Similarity	NPC476944
0.8562	High Similarity	NPC475226
0.8554	High Similarity	NPC471437
0.8545	High Similarity	NPC285227
0.8544	High Similarity	NPC57998
0.8535	High Similarity	NPC291150
0.8529	High Similarity	NPC242068
0.8529	High Similarity	NPC247563
0.8528	High Similarity	NPC121995
0.8528	High Similarity	NPC149945
0.8528	High Similarity	NPC472141
0.8526	High Similarity	NPC472654
0.8526	High Similarity	NPC195325
0.8519	High Similarity	NPC165218
0.8519	High Similarity	NPC88841
0.8519	High Similarity	NPC471168
0.8519	High Similarity	NPC472669
0.8519	High Similarity	NPC476035
0.8519	High Similarity	NPC14499
0.8519	High Similarity	NPC288602
0.8519	High Similarity	NPC472139
0.8519	High Similarity	NPC475039
0.8516	High Similarity	NPC255414
0.8516	High Similarity	NPC71821
0.8516	High Similarity	NPC250228
0.8509	High Similarity	NPC287559
0.8506	High Similarity	NPC41182
0.8506	High Similarity	NPC34056
0.8503	High Similarity	NPC262386
0.85	High Similarity	NPC197137
0.8497	Intermediate Similarity	NPC470741
0.8487	Intermediate Similarity	NPC20500
0.8485	Intermediate Similarity	NPC470995
0.8481	Intermediate Similarity	NPC182427
0.8481	Intermediate Similarity	NPC322546
0.8481	Intermediate Similarity	NPC246164
0.8481	Intermediate Similarity	NPC308205

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 NPC472283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	1029
0.2-0.3	2176
0.3-0.4	2691
0.4-0.5	1790
0.5-0.6	830
0.6-0.7	252
0.7-0.8	39
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
0.8625	High Similarity	NPD5537	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD8434	Phase 2
0.8148	Intermediate Similarity	NPD5760	Phase 2
0.8148	Intermediate Similarity	NPD5761	Phase 2
0.7759	Intermediate Similarity	NPD6764	Approved
0.7759	Intermediate Similarity	NPD6765	Approved
0.7605	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6785	Approved
0.7584	Intermediate Similarity	NPD6784	Approved
0.7574	Intermediate Similarity	NPD7075	Discontinued
0.7547	Intermediate Similarity	NPD1471	Phase 3
0.753	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD7819	Suspended
0.7485	Intermediate Similarity	NPD5494	Approved
0.7442	Intermediate Similarity	NPD1247	Approved
0.7427	Intermediate Similarity	NPD919	Approved
0.7353	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD920	Approved
0.7337	Intermediate Similarity	NPD6801	Discontinued
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7411	Suspended
0.7273	Intermediate Similarity	NPD6799	Approved
0.7263	Intermediate Similarity	NPD6559	Discontinued
0.7251	Intermediate Similarity	NPD5402	Approved
0.7251	Intermediate Similarity	NPD3817	Phase 2
0.7232	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4628	Phase 3
0.7191	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD8404	Phase 2
0.716	Intermediate Similarity	NPD3226	Approved
0.7143	Intermediate Similarity	NPD5403	Approved
0.7135	Intermediate Similarity	NPD7799	Discontinued
0.7126	Intermediate Similarity	NPD5401	Approved
0.7119	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD8312	Approved
0.7088	Intermediate Similarity	NPD8313	Approved
0.7069	Intermediate Similarity	NPD3749	Approved
0.7065	Intermediate Similarity	NPD8150	Discontinued
0.7062	Intermediate Similarity	NPD3926	Phase 2
0.7055	Intermediate Similarity	NPD2796	Approved
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.703	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4380	Phase 2
0.7016	Intermediate Similarity	NPD4107	Approved
0.7012	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3882	Suspended
0.7006	Intermediate Similarity	NPD7236	Approved
0.7	Intermediate Similarity	NPD5844	Phase 1
0.6994	Remote Similarity	NPD3748	Approved
0.6983	Remote Similarity	NPD7473	Discontinued
0.6971	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD8285	Discontinued
0.694	Remote Similarity	NPD7808	Phase 3
0.694	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1243	Approved
0.6927	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6166	Phase 2
0.6927	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6832	Phase 2
0.6909	Remote Similarity	NPD2346	Discontinued
0.6901	Remote Similarity	NPD7239	Suspended
0.6897	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4482	Phase 3
0.6886	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7251	Discontinued
0.6882	Remote Similarity	NPD6273	Approved
0.6865	Remote Similarity	NPD8407	Phase 2
0.686	Remote Similarity	NPD7458	Discontinued
0.6854	Remote Similarity	NPD6959	Discontinued
0.6851	Remote Similarity	NPD3818	Discontinued
0.6851	Remote Similarity	NPD3751	Discontinued
0.6842	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1934	Approved
0.6835	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2403	Approved
0.6833	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6797	Phase 2
0.6824	Remote Similarity	NPD2533	Approved
0.6824	Remote Similarity	NPD2534	Approved
0.6824	Remote Similarity	NPD2532	Approved
0.6821	Remote Similarity	NPD7435	Discontinued
0.6818	Remote Similarity	NPD7768	Phase 2
0.6816	Remote Similarity	NPD6232	Discontinued
0.6816	Remote Similarity	NPD6808	Phase 2
0.681	Remote Similarity	NPD6355	Discontinued
0.6809	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD8368	Discontinued
0.679	Remote Similarity	NPD8032	Phase 2
0.6788	Remote Similarity	NPD2799	Discontinued
0.6786	Remote Similarity	NPD3750	Approved
0.678	Remote Similarity	NPD7907	Approved
0.6776	Remote Similarity	NPD7074	Phase 3
0.6766	Remote Similarity	NPD1549	Phase 2
0.6763	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3887	Approved
0.673	Remote Similarity	NPD3266	Approved
0.673	Remote Similarity	NPD3267	Approved
0.6726	Remote Similarity	NPD2800	Approved
0.6722	Remote Similarity	NPD3787	Discontinued
0.6721	Remote Similarity	NPD7054	Approved
0.6715	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7874	Approved
0.67	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7472	Approved
0.665	Remote Similarity	NPD7698	Approved
0.665	Remote Similarity	NPD7696	Phase 3
0.665	Remote Similarity	NPD7697	Approved
0.6648	Remote Similarity	NPD37	Approved
0.6647	Remote Similarity	NPD1551	Phase 2
0.6647	Remote Similarity	NPD6100	Approved
0.6647	Remote Similarity	NPD6099	Approved
0.6646	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8435	Approved
0.6629	Remote Similarity	NPD4966	Approved
0.6629	Remote Similarity	NPD4967	Phase 2
0.6629	Remote Similarity	NPD4965	Approved
0.6628	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2313	Discontinued
0.6626	Remote Similarity	NPD3268	Approved
0.6616	Remote Similarity	NPD7871	Phase 2
0.6616	Remote Similarity	NPD8320	Phase 1
0.6616	Remote Similarity	NPD8319	Approved
0.6616	Remote Similarity	NPD7870	Phase 2
0.6613	Remote Similarity	NPD7685	Pre-registration
0.661	Remote Similarity	NPD1465	Phase 2
0.661	Remote Similarity	NPD8455	Phase 2
0.661	Remote Similarity	NPD2801	Approved
0.6607	Remote Similarity	NPD5763	Approved
0.6607	Remote Similarity	NPD5762	Approved
0.6607	Remote Similarity	NPD2344	Approved
0.6606	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1933	Approved
0.6599	Remote Similarity	NPD3057	Approved
0.6598	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5890	Approved
0.6591	Remote Similarity	NPD5889	Approved
0.6582	Remote Similarity	NPD6777	Approved
0.6582	Remote Similarity	NPD6781	Approved
0.6582	Remote Similarity	NPD6782	Approved
0.6582	Remote Similarity	NPD6780	Approved
0.6582	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6776	Approved
0.6582	Remote Similarity	NPD6779	Approved
0.6582	Remote Similarity	NPD6778	Approved
0.6576	Remote Similarity	NPD7228	Approved
0.6568	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD17	Approved
0.6556	Remote Similarity	NPD6234	Discontinued
0.6548	Remote Similarity	NPD2935	Discontinued
0.6548	Remote Similarity	NPD2438	Suspended
0.6545	Remote Similarity	NPD8360	Approved
0.6545	Remote Similarity	NPD8361	Approved
0.6541	Remote Similarity	NPD3972	Approved
0.6538	Remote Similarity	NPD7229	Phase 3
0.6536	Remote Similarity	NPD7057	Phase 3
0.6536	Remote Similarity	NPD7058	Phase 2
0.6527	Remote Similarity	NPD7097	Phase 1
0.6526	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6798	Discontinued
0.6522	Remote Similarity	NPD4665	Approved
0.6522	Remote Similarity	NPD4111	Phase 1
0.6517	Remote Similarity	NPD7701	Phase 2
0.6515	Remote Similarity	NPD3533	Approved
0.6515	Remote Similarity	NPD2972	Approved
0.6509	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2353	Approved
0.6505	Remote Similarity	NPD5980	Discovery
0.6502	Remote Similarity	NPD7801	Approved
0.6494	Remote Similarity	NPD1512	Approved
0.6491	Remote Similarity	NPD8166	Discontinued
0.6491	Remote Similarity	NPD7003	Approved
0.6488	Remote Similarity	NPD1510	Phase 2
0.6488	Remote Similarity	NPD7033	Discontinued
0.6485	Remote Similarity	NPD6233	Phase 2
0.6484	Remote Similarity	NPD7199	Phase 2
0.648	Remote Similarity	NPD5353	Approved
0.648	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2897	Discontinued
0.6463	Remote Similarity	NPD7095	Approved
0.6456	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD2968	Approved
0.6455	Remote Similarity	NPD2971	Approved
0.6453	Remote Similarity	NPD2309	Approved
0.6452	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD5711	Approved
0.6448	Remote Similarity	NPD5710	Approved
0.6446	Remote Similarity	NPD4307	Phase 2
0.6441	Remote Similarity	NPD6585	Discontinued
0.6438	Remote Similarity	NPD1608	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