NPASS Compound

Structure

NPC476224 OpenBabel07101718302D 46 50 0 0 1 0 0 0 0 0999 V2000 -0.9176 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7864 0.8612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3668 -1.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4969 -4.2581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1348 -2.0101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6348 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6158 -0.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1349 -0.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6524 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6245 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6245 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4623 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1245 0.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0824 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9204 1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3668 -0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2322 -3.2938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3155 0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 -1.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9204 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2054 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 -0.1388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3644 0.3601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6348 -0.4739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4739 -0.4739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6348 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4739 -1.1441 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6702 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6702 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9204 2.3612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2328 0.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7353 -3.0409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9204 -3.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9975 2.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3827 -2.5419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7864 -2.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9335 0.0511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 0.8612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5008 0.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1565 1.3383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9350 -2.5824 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 16 2 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 9 40 1 0 0 0 0 10 11 2 0 0 0 0 10 20 1 0 0 0 0 11 41 1 0 0 0 0 12 21 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 20 2 0 0 0 0 14 41 1 0 0 0 0 15 30 1 0 0 0 0 15 32 1 0 0 0 0 16 32 1 0 0 0 0 16 33 1 0 0 0 0 17 34 2 0 0 0 0 17 42 1 0 0 0 0 18 35 2 0 0 0 0 18 43 1 0 0 0 0 19 36 2 0 0 0 0 19 45 1 0 0 0 0 20 25 1 0 0 0 0 21 29 1 0 0 0 0 21 31 1 1 0 0 0 22 37 2 0 0 0 0 22 40 1 0 0 0 0 23 38 2 0 0 0 0 23 44 1 0 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 24 42 1 6 0 0 0 25 30 1 1 0 0 0 25 44 1 0 0 0 0 26 29 1 0 0 0 0 26 43 1 6 0 0 0 27 31 1 6 0 0 0 27 46 1 0 0 0 0 28 31 1 0 0 0 0 28 32 1 0 0 0 0 28 39 2 0 0 0 0 30 33 1 1 0 0 0 31 8 1 1 0 0 0 32 45 1 1 0 0 0 33 13 1 1 0 0 0 33 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	644.25
Volume:	627.086
LogP:	2.919
LogD:	1.601
LogS:	-4.697
# Rotatable Bonds:	10
TPSA:	170.94
# H-Bond Aceptor:	13
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	6.653
Fsp3:	0.636
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:	-5.294
MDCK Permeability:	6.33997842669487e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.914
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.378
Plasma Protein Binding (PPB):	69.80554962158203%
Volume Distribution (VD):	1.495
Pgp-substrate:	32.48003005981445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.136
CYP2C9-inhibitor:	0.171
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.316
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.868

ADMET: Excretion

Clearance (CL):	2.5
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.895
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.412
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.636
Skin Sensitization:	0.084
Carcinogencity:	0.258
Eye Corrosion:	0.088
Eye Irritation:	0.04
Respiratory Toxicity:	0.517

Download Data

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

Natural Product: NPC476224

Natural Product ID:	NPC476224
*Common Name:**	Cineracipadesin F
IUPAC Name:	n.a.
Synonyms:	Cineracipadesin F
Standard InCHIKey:	AFXJIFZZYGMEIG-FZJICGSQSA-N
Standard InCHI:	InChI=1S/C33H40O13/c1-16-32(45-19(4)36)15-30(7)25(20-10-11-41-14-20)44-23(38)13-33(16,30)46-27-24(42-17(2)34)26(43-18(3)35)29(5,6)21(12-22(37)40-9)31(27,8)28(32)39/h10-11,14,21,24-27H,1,12-13,15H2,2-9H3/t21-,24-,25-,26+,27-,30-,31+,32+,33-/m0/s1
SMILES:	COC(=O)C[C@@H]1[C@]2(C)[C@@H](O[C@]34C(=C)[C@](C2=O)(OC(=O)C)C[C@@]4(C)[C@@H](OC(=O)C3)c2cocc2)[C@H]([C@H](C1(C)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL555925
PubChem CID:	42639972
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
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17655260]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[19296669]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	Longlin County of Guangxi Province, China	2012-JUL	PMID[25970729]
NPO4584	Cipadessa cinerascens	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[568633]

☑ 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 NPC476224 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	444
0.1-0.2	1628
0.2-0.3	3588
0.3-0.4	6760
0.4-0.5	11442
0.5-0.6	9342
0.6-0.7	8191
0.7-0.8	982
0.8-0.85	241
0.85-0.9	65
0.9-0.95	6
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9742	High Similarity	NPC6326
0.9548	High Similarity	NPC195131
0.9497	High Similarity	NPC472764
0.9484	High Similarity	NPC204663
0.9437	High Similarity	NPC472765
0.9437	High Similarity	NPC472766
0.9434	High Similarity	NPC149945
0.9317	High Similarity	NPC327922
0.9245	High Similarity	NPC472767
0.9187	High Similarity	NPC472669
0.9177	High Similarity	NPC167142
0.9146	High Similarity	NPC469848
0.9125	High Similarity	NPC471166
0.9125	High Similarity	NPC471167
0.9096	High Similarity	NPC478177
0.9091	High Similarity	NPC94763
0.9091	High Similarity	NPC236004
0.9091	High Similarity	NPC471632
0.9006	High Similarity	NPC472668
0.9	High Similarity	NPC237155
0.897	High Similarity	NPC285227
0.8951	High Similarity	NPC471168
0.8944	High Similarity	NPC191828
0.8938	High Similarity	NPC472283
0.8909	High Similarity	NPC472659
0.8902	High Similarity	NPC472775
0.8902	High Similarity	NPC472774
0.8889	High Similarity	NPC472771
0.8889	High Similarity	NPC197596
0.8889	High Similarity	NPC470939
0.8862	High Similarity	NPC471437
0.8841	High Similarity	NPC478178
0.8834	High Similarity	NPC469846
0.8834	High Similarity	NPC472773
0.8834	High Similarity	NPC165218
0.881	High Similarity	NPC469633
0.8797	High Similarity	NPC156189
0.8788	High Similarity	NPC476853
0.878	High Similarity	NPC469849
0.8765	High Similarity	NPC477403
0.8758	High Similarity	NPC175964
0.8758	High Similarity	NPC263265
0.8758	High Similarity	NPC126723
0.8758	High Similarity	NPC471169
0.8757	High Similarity	NPC470181
0.875	High Similarity	NPC469576
0.8743	High Similarity	NPC159232
0.8735	High Similarity	NPC160651
0.8735	High Similarity	NPC472652
0.8734	High Similarity	NPC470790
0.8734	High Similarity	NPC470791
0.8727	High Similarity	NPC470875
0.8721	High Similarity	NPC247563
0.8721	High Similarity	NPC105395
0.8721	High Similarity	NPC242068
0.872	High Similarity	NPC469338
0.872	High Similarity	NPC292389
0.872	High Similarity	NPC476197
0.8712	High Similarity	NPC470789
0.8712	High Similarity	NPC472653
0.8712	High Similarity	NPC25255
0.8712	High Similarity	NPC305016
0.8704	High Similarity	NPC286722
0.8704	High Similarity	NPC472772
0.8696	High Similarity	NPC476262
0.8696	High Similarity	NPC471175
0.8688	High Similarity	NPC29695
0.8688	High Similarity	NPC182427
0.8688	High Similarity	NPC476201
0.8675	High Similarity	NPC476850
0.8675	High Similarity	NPC478179
0.8675	High Similarity	NPC472651
0.8675	High Similarity	NPC476861
0.8675	High Similarity	NPC173516
0.8667	High Similarity	NPC470940
0.8667	High Similarity	NPC476856
0.8667	High Similarity	NPC276551
0.8667	High Similarity	NPC476858
0.8667	High Similarity	NPC123088
0.8667	High Similarity	NPC476860
0.8667	High Similarity	NPC476857
0.8659	High Similarity	NPC329938
0.8659	High Similarity	NPC193798
0.8659	High Similarity	NPC82851
0.8655	High Similarity	NPC470938
0.865	High Similarity	NPC473473
0.865	High Similarity	NPC474932
0.865	High Similarity	NPC475295
0.8642	High Similarity	NPC209364
0.8642	High Similarity	NPC107646
0.8642	High Similarity	NPC60973
0.8625	High Similarity	NPC116717
0.8625	High Similarity	NPC18135
0.8623	High Similarity	NPC471397
0.8616	High Similarity	NPC329180
0.8614	High Similarity	NPC23387
0.8614	High Similarity	NPC214600
0.8608	High Similarity	NPC470941
0.8606	High Similarity	NPC224394
0.8606	High Similarity	NPC477405
0.8606	High Similarity	NPC663
0.8598	High Similarity	NPC475381
0.8598	High Similarity	NPC477402
0.8589	High Similarity	NPC45101
0.8589	High Similarity	NPC469847
0.858	High Similarity	NPC264943
0.858	High Similarity	NPC469850
0.8571	High Similarity	NPC84063
0.8563	High Similarity	NPC472282
0.8563	High Similarity	NPC473766
0.8563	High Similarity	NPC473753
0.8562	High Similarity	NPC196864
0.8562	High Similarity	NPC159927
0.8562	High Similarity	NPC477404
0.8562	High Similarity	NPC469335
0.8545	High Similarity	NPC69028
0.8544	High Similarity	NPC262198
0.8537	High Similarity	NPC472779
0.8537	High Similarity	NPC475226
0.8537	High Similarity	NPC475967
0.8529	High Similarity	NPC477824
0.8512	High Similarity	NPC271235
0.8494	Intermediate Similarity	NPC302369
0.8494	Intermediate Similarity	NPC134254
0.8494	Intermediate Similarity	NPC39986
0.848	Intermediate Similarity	NPC167340
0.8476	Intermediate Similarity	NPC249021
0.8476	Intermediate Similarity	NPC475066
0.8476	Intermediate Similarity	NPC36655
0.8476	Intermediate Similarity	NPC173544
0.8476	Intermediate Similarity	NPC261597
0.8466	Intermediate Similarity	NPC44675
0.8466	Intermediate Similarity	NPC214541
0.8462	Intermediate Similarity	NPC470995
0.8462	Intermediate Similarity	NPC472650
0.8457	Intermediate Similarity	NPC308205
0.8457	Intermediate Similarity	NPC322546
0.8447	Intermediate Similarity	NPC476122
0.8447	Intermediate Similarity	NPC46551
0.8443	Intermediate Similarity	NPC259943
0.8434	Intermediate Similarity	NPC5079
0.8434	Intermediate Similarity	NPC5741
0.8434	Intermediate Similarity	NPC263432
0.8418	Intermediate Similarity	NPC86935
0.8415	Intermediate Similarity	NPC469485
0.8402	Intermediate Similarity	NPC472673
0.8395	Intermediate Similarity	NPC291150
0.8383	Intermediate Similarity	NPC51568
0.8383	Intermediate Similarity	NPC234660
0.8375	Intermediate Similarity	NPC221809
0.8373	Intermediate Similarity	NPC335761
0.8365	Intermediate Similarity	NPC34056
0.8364	Intermediate Similarity	NPC472776
0.8364	Intermediate Similarity	NPC472778
0.8364	Intermediate Similarity	NPC470118
0.8364	Intermediate Similarity	NPC299038
0.8364	Intermediate Similarity	NPC197137
0.8364	Intermediate Similarity	NPC472777
0.8364	Intermediate Similarity	NPC187149
0.8354	Intermediate Similarity	NPC469336
0.8333	Intermediate Similarity	NPC271657
0.8333	Intermediate Similarity	NPC261184
0.8333	Intermediate Similarity	NPC5180
0.8323	Intermediate Similarity	NPC117986
0.8323	Intermediate Similarity	NPC18347
0.8323	Intermediate Similarity	NPC149896
0.8323	Intermediate Similarity	NPC200782
0.8313	Intermediate Similarity	NPC472671
0.8304	Intermediate Similarity	NPC160818
0.8304	Intermediate Similarity	NPC169299
0.8293	Intermediate Similarity	NPC282445
0.8293	Intermediate Similarity	NPC178932
0.8284	Intermediate Similarity	NPC472141
0.8274	Intermediate Similarity	NPC14499
0.8274	Intermediate Similarity	NPC475039
0.8274	Intermediate Similarity	NPC476035
0.8274	Intermediate Similarity	NPC472139
0.8272	Intermediate Similarity	NPC472654
0.8272	Intermediate Similarity	NPC471001
0.8263	Intermediate Similarity	NPC333139
0.8261	Intermediate Similarity	NPC255414
0.8253	Intermediate Similarity	NPC214495
0.8253	Intermediate Similarity	NPC470119
0.8246	Intermediate Similarity	NPC302392
0.8246	Intermediate Similarity	NPC82602
0.8242	Intermediate Similarity	NPC92979
0.8239	Intermediate Similarity	NPC80635
0.8239	Intermediate Similarity	NPC223415
0.8232	Intermediate Similarity	NPC469503
0.8232	Intermediate Similarity	NPC472672
0.8232	Intermediate Similarity	NPC75906
0.8225	Intermediate Similarity	NPC470182
0.8225	Intermediate Similarity	NPC27541
0.8225	Intermediate Similarity	NPC62692
0.8225	Intermediate Similarity	NPC126984
0.8214	Intermediate Similarity	NPC290400
0.8214	Intermediate Similarity	NPC96443
0.8214	Intermediate Similarity	NPC470792
0.8214	Intermediate Similarity	NPC188649
0.8204	Intermediate Similarity	NPC473368

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 NPC476224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	1065
0.2-0.3	2439
0.3-0.4	2714
0.4-0.5	1703
0.5-0.6	653
0.6-0.7	192
0.7-0.8	9
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
0.8354	Intermediate Similarity	NPD5760	Phase 2
0.8354	Intermediate Similarity	NPD5761	Phase 2
0.8263	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD8434	Phase 2
0.7753	Intermediate Similarity	NPD6764	Approved
0.7753	Intermediate Similarity	NPD6765	Approved
0.7582	Intermediate Similarity	NPD6785	Approved
0.7582	Intermediate Similarity	NPD6784	Approved
0.7345	Intermediate Similarity	NPD1247	Approved
0.733	Intermediate Similarity	NPD919	Approved
0.7204	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7075	Discontinued
0.7151	Intermediate Similarity	NPD920	Approved
0.7126	Intermediate Similarity	NPD6599	Discontinued
0.7102	Intermediate Similarity	NPD7819	Suspended
0.7095	Intermediate Similarity	NPD5494	Approved
0.7049	Intermediate Similarity	NPD7799	Discontinued
0.7035	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1471	Phase 3
0.6977	Remote Similarity	NPD6799	Approved
0.6966	Remote Similarity	NPD3817	Phase 2
0.6949	Remote Similarity	NPD6801	Discontinued
0.6919	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3926	Phase 2
0.6872	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8404	Phase 2
0.6839	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3882	Suspended
0.6821	Remote Similarity	NPD7236	Approved
0.6809	Remote Similarity	NPD7685	Pre-registration
0.6809	Remote Similarity	NPD6559	Discontinued
0.6798	Remote Similarity	NPD7411	Suspended
0.6793	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5402	Approved
0.6776	Remote Similarity	NPD8127	Discontinued
0.6774	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2403	Approved
0.6744	Remote Similarity	NPD1243	Approved
0.6738	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7239	Suspended
0.6705	Remote Similarity	NPD4628	Phase 3
0.6703	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5401	Approved
0.6648	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD7473	Discontinued
0.663	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6002	Phase 3
0.6628	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5763	Approved
0.6628	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5762	Approved
0.6628	Remote Similarity	NPD6005	Phase 3
0.6628	Remote Similarity	NPD6004	Phase 3
0.6628	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6273	Approved
0.6608	Remote Similarity	NPD2799	Discontinued
0.6597	Remote Similarity	NPD7808	Phase 3
0.6597	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3818	Discontinued
0.6595	Remote Similarity	NPD7199	Phase 2
0.6592	Remote Similarity	NPD3226	Approved
0.6584	Remote Similarity	NPD7497	Discontinued
0.6578	Remote Similarity	NPD6166	Phase 2
0.6578	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD1934	Approved
0.6573	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5844	Phase 1
0.6556	Remote Similarity	NPD4380	Phase 2
0.6554	Remote Similarity	NPD2532	Approved
0.6554	Remote Similarity	NPD2533	Approved
0.6554	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2534	Approved
0.6552	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD8150	Discontinued
0.6545	Remote Similarity	NPD7251	Discontinued
0.6529	Remote Similarity	NPD6355	Discontinued
0.6528	Remote Similarity	NPD8407	Phase 2
0.6527	Remote Similarity	NPD6832	Phase 2
0.6522	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4107	Approved
0.6514	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD3751	Discontinued
0.6492	Remote Similarity	NPD6797	Phase 2
0.6479	Remote Similarity	NPD7907	Approved
0.6477	Remote Similarity	NPD8312	Approved
0.6477	Remote Similarity	NPD3887	Approved
0.6477	Remote Similarity	NPD8313	Approved
0.6471	Remote Similarity	NPD6232	Discontinued
0.6471	Remote Similarity	NPD3787	Discontinued
0.6471	Remote Similarity	NPD6808	Phase 2
0.6471	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD8285	Discontinued
0.6461	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD8368	Discontinued
0.6457	Remote Similarity	NPD2800	Approved
0.6446	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.644	Remote Similarity	NPD7074	Phase 3
0.6422	Remote Similarity	NPD7435	Discontinued
0.6416	Remote Similarity	NPD3748	Approved
0.6413	Remote Similarity	NPD5353	Approved
0.6412	Remote Similarity	NPD8032	Phase 2
0.6404	Remote Similarity	NPD4482	Phase 3
0.6402	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1549	Phase 2
0.64	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7054	Approved
0.6378	Remote Similarity	NPD7057	Phase 3
0.6378	Remote Similarity	NPD4967	Phase 2
0.6378	Remote Similarity	NPD4966	Approved
0.6378	Remote Similarity	NPD7058	Phase 2
0.6378	Remote Similarity	NPD7768	Phase 2
0.6378	Remote Similarity	NPD4965	Approved
0.6359	Remote Similarity	NPD2801	Approved
0.6354	Remote Similarity	NPD7472	Approved
0.6343	Remote Similarity	NPD2346	Discontinued
0.6343	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6959	Discontinued
0.6316	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7874	Approved
0.631	Remote Similarity	NPD5647	Approved
0.631	Remote Similarity	NPD6234	Discontinued
0.631	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD37	Approved
0.6301	Remote Similarity	NPD6653	Approved
0.6286	Remote Similarity	NPD6100	Approved
0.6286	Remote Similarity	NPD1551	Phase 2
0.6286	Remote Similarity	NPD6099	Approved
0.6284	Remote Similarity	NPD7028	Phase 2
0.6278	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.627	Remote Similarity	NPD1465	Phase 2
0.6267	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7698	Approved
0.6262	Remote Similarity	NPD7697	Approved
0.6262	Remote Similarity	NPD7696	Phase 3
0.6257	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2353	Approved
0.625	Remote Similarity	NPD3267	Approved
0.625	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7228	Approved
0.625	Remote Similarity	NPD3266	Approved
0.625	Remote Similarity	NPD2163	Approved
0.625	Remote Similarity	NPD2344	Approved
0.6243	Remote Similarity	NPD1933	Approved
0.6243	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD1512	Approved
0.6243	Remote Similarity	NPD447	Suspended
0.6236	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD3750	Approved
0.6233	Remote Similarity	NPD4665	Approved
0.6233	Remote Similarity	NPD4111	Phase 1
0.6232	Remote Similarity	NPD7870	Phase 2
0.6232	Remote Similarity	NPD8320	Phase 1
0.6232	Remote Similarity	NPD8319	Approved
0.6232	Remote Similarity	NPD7871	Phase 2
0.6231	Remote Similarity	NPD8435	Approved
0.6231	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7458	Discontinued
0.6229	Remote Similarity	NPD7033	Discontinued
0.6211	Remote Similarity	NPD7315	Approved
0.6211	Remote Similarity	NPD5711	Approved
0.6211	Remote Similarity	NPD7229	Phase 3
0.6211	Remote Similarity	NPD5710	Approved
0.6207	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD6190	Approved
0.6195	Remote Similarity	NPD6777	Approved
0.6195	Remote Similarity	NPD6782	Approved
0.6195	Remote Similarity	NPD6779	Approved
0.6195	Remote Similarity	NPD6778	Approved
0.6195	Remote Similarity	NPD6780	Approved
0.6195	Remote Similarity	NPD6781	Approved
0.6195	Remote Similarity	NPD6776	Approved
0.6193	Remote Similarity	NPD2935	Discontinued
0.619	Remote Similarity	NPD1876	Approved
0.6182	Remote Similarity	NPD17	Approved
0.6178	Remote Similarity	NPD5242	Approved
0.6163	Remote Similarity	NPD3268	Approved
0.6163	Remote Similarity	NPD2313	Discontinued
0.6162	Remote Similarity	NPD6385	Approved
0.6162	Remote Similarity	NPD6386	Approved
0.6154	Remote Similarity	NPD5953	Discontinued
0.615	Remote Similarity	NPD8360	Approved
0.615	Remote Similarity	NPD8361	Approved
0.6145	Remote Similarity	NPD4110	Phase 3
0.6145	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD7701	Phase 2
0.6141	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD1510	Phase 2
0.6135	Remote Similarity	NPD3057	Approved
0.6134	Remote Similarity	NPD7286	Phase 2
0.6133	Remote Similarity	NPD1511	Approved
0.6133	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7801	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