NPASS Compound

Structure

NPC476122 OpenBabel07101718242D 41 45 0 0 1 0 0 0 0 0999 V2000 -2.2448 -0.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3985 3.8852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8248 3.7782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3677 3.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6068 3.0610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1404 0.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3217 0.2658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2107 5.4007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8795 -0.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5334 0.3050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2373 3.0277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6224 1.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2941 0.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5522 -1.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0889 0.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3985 -0.0237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3985 2.9080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6322 3.2277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9867 -0.0237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5522 1.4421 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6224 1.9267 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6787 1.8292 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0563 0.7512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1642 4.0022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2941 -1.9782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3985 0.9535 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1404 -0.5124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0563 2.2536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2941 -0.0237 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6787 1.1755 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5522 -0.5124 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2448 2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5126 3.6517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9717 4.5527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2941 -2.9555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2838 4.4262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0448 1.1513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5522 2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5592 2.2532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1404 -1.4896 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 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 8 36 1 0 0 0 0 9 10 2 0 0 0 0 9 19 1 0 0 0 0 10 37 1 0 0 0 0 11 21 1 0 0 0 0 11 24 1 0 0 0 0 12 22 1 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 29 1 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 15 37 1 0 0 0 0 16 26 1 0 0 0 0 16 31 1 0 0 0 0 17 32 2 0 0 0 0 17 38 1 0 0 0 0 18 33 2 0 0 0 0 18 39 1 0 0 0 0 19 27 1 0 0 0 0 20 26 1 0 0 0 0 20 38 1 6 0 0 0 21 28 1 0 0 0 0 21 30 1 1 0 0 0 22 28 1 0 0 0 0 22 39 1 6 0 0 0 23 30 1 6 0 0 0 23 41 1 0 0 0 0 24 34 2 0 0 0 0 24 36 1 0 0 0 0 25 35 2 0 0 0 0 25 40 1 0 0 0 0 26 30 1 1 0 0 0 27 29 1 6 0 0 0 27 40 1 0 0 0 0 29 31 1 6 0 0 0 30 7 1 1 0 0 0 31 14 1 1 0 0 0 31 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.26
Volume:	571.397
LogP:	4.224
LogD:	2.904
LogS:	-5.204
# Rotatable Bonds:	8
TPSA:	127.57
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.283
Synthetic Accessibility Score:	6.452
Fsp3:	0.677
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:	-5.261
MDCK Permeability:	8.505715959472582e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.297
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.717
Plasma Protein Binding (PPB):	68.9507064819336%
Volume Distribution (VD):	1.444
Pgp-substrate:	29.471359252929688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.178
CYP2C9-inhibitor:	0.361
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.748
CYP3A4-substrate:	0.573

ADMET: Excretion

Clearance (CL):	7.268
Half-life (T1/2):	0.433

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.689
Drug-inuced Liver Injury (DILI):	0.758
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.116
Carcinogencity:	0.184
Eye Corrosion:	0.049
Eye Irritation:	0.032
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC476122

Natural Product ID:	NPC476122
*Common Name:**	Cineracipadesin D
IUPAC Name:	n.a.
Synonyms:	Cineracipadesin D
Standard InCHIKey:	VYCLTUNEIJAHFU-VPJGEXDESA-N
Standard InCHI:	InChI=1S/C31H40O10/c1-16-26-20(38-17(2)32)13-29(6)27(19-9-10-37-15-19)40-25(35)14-31(16,29)41-23-12-22(39-18(3)33)28(4,5)21(30(23,26)7)11-24(34)36-8/h9-10,15,20-23,26-27H,1,11-14H2,2-8H3/t20-,21+,22-,23+,26-,27+,29+,30-,31+/m1/s1
SMILES:	CC(=O)OC1CC2C(C(C1(C)C)CC(=O)OC)(C3C(CC4(C(OC(=O)CC4(C3=C)O2)C5=COC=C5)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL538140
PubChem CID:	42639821
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic 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[554088]

☑ 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 NPC476122 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	422
0.1-0.2	1508
0.2-0.3	3220
0.3-0.4	6106
0.4-0.5	10480
0.5-0.6	9918
0.6-0.7	8976
0.7-0.8	1641
0.8-0.85	273
0.85-0.9	115
0.9-0.95	32
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC476262
0.9724	High Similarity	NPC476201
0.9658	High Similarity	NPC282445
0.9586	High Similarity	NPC477404
0.9586	High Similarity	NPC196864
0.9514	High Similarity	NPC470941
0.9463	High Similarity	NPC249021
0.9456	High Similarity	NPC469503
0.9452	High Similarity	NPC469335
0.9452	High Similarity	NPC159927
0.9404	High Similarity	NPC200782
0.9329	High Similarity	NPC469850
0.9276	High Similarity	NPC82851
0.9272	High Similarity	NPC475295
0.9272	High Similarity	NPC473473
0.9247	High Similarity	NPC221809
0.9205	High Similarity	NPC286722
0.9205	High Similarity	NPC167142
0.9205	High Similarity	NPC472772
0.92	High Similarity	NPC469336
0.9156	High Similarity	NPC470182
0.915	High Similarity	NPC470939
0.9139	High Similarity	NPC126723
0.9139	High Similarity	NPC107646
0.9139	High Similarity	NPC209364
0.9133	High Similarity	NPC178932
0.9128	High Similarity	NPC18135
0.9097	High Similarity	NPC93172
0.9097	High Similarity	NPC97574
0.9091	High Similarity	NPC134254
0.9091	High Similarity	NPC302369
0.9091	High Similarity	NPC39986
0.9091	High Similarity	NPC419
0.9091	High Similarity	NPC477405
0.9091	High Similarity	NPC476197
0.9091	High Similarity	NPC469846
0.9085	High Similarity	NPC475381
0.9079	High Similarity	NPC472283
0.906	High Similarity	NPC156189
0.9034	High Similarity	NPC121158
0.9032	High Similarity	NPC271657
0.9026	High Similarity	NPC18347
0.9026	High Similarity	NPC149896
0.9026	High Similarity	NPC472771
0.9021	High Similarity	NPC476943
0.9007	High Similarity	NPC57998
0.9007	High Similarity	NPC30222
0.8993	High Similarity	NPC470790
0.8993	High Similarity	NPC470791
0.8986	High Similarity	NPC255414
0.8968	High Similarity	NPC472773
0.8968	High Similarity	NPC469338
0.8968	High Similarity	NPC234660
0.8968	High Similarity	NPC51568
0.8968	High Similarity	NPC292389
0.8961	High Similarity	NPC335761
0.8961	High Similarity	NPC305016
0.8961	High Similarity	NPC472653
0.8954	High Similarity	NPC299038
0.8954	High Similarity	NPC45101
0.8951	High Similarity	NPC310830
0.8947	High Similarity	NPC35000
0.8947	High Similarity	NPC264943
0.8919	High Similarity	NPC262198
0.8917	High Similarity	NPC472775
0.8917	High Similarity	NPC173516
0.8917	High Similarity	NPC472774
0.8912	High Similarity	NPC251865
0.8912	High Similarity	NPC476944
0.8912	High Similarity	NPC142113
0.891	High Similarity	NPC469849
0.891	High Similarity	NPC476856
0.891	High Similarity	NPC276551
0.891	High Similarity	NPC476858
0.891	High Similarity	NPC470940
0.891	High Similarity	NPC476857
0.8903	High Similarity	NPC211777
0.8903	High Similarity	NPC5079
0.8903	High Similarity	NPC207978
0.8903	High Similarity	NPC69028
0.8896	High Similarity	NPC237155
0.8896	High Similarity	NPC475967
0.8896	High Similarity	NPC474611
0.8896	High Similarity	NPC307383
0.8889	High Similarity	NPC204663
0.8889	High Similarity	NPC60973
0.8867	High Similarity	NPC125182
0.8867	High Similarity	NPC195325
0.8867	High Similarity	NPC69647
0.8867	High Similarity	NPC472654
0.8861	High Similarity	NPC471397
0.8861	High Similarity	NPC160651
0.8861	High Similarity	NPC271235
0.8854	High Similarity	NPC470875
0.8854	High Similarity	NPC472141
0.8851	High Similarity	NPC41182
0.8846	High Similarity	NPC165218
0.8846	High Similarity	NPC472139
0.8846	High Similarity	NPC198047
0.8844	High Similarity	NPC223415
0.8839	High Similarity	NPC25255
0.8831	High Similarity	NPC36655
0.8831	High Similarity	NPC195131
0.8831	High Similarity	NPC261597
0.8824	High Similarity	NPC44675
0.8824	High Similarity	NPC214541
0.8819	High Similarity	NPC310043
0.8805	High Similarity	NPC82602
0.88	High Similarity	NPC19747
0.8797	High Similarity	NPC476850
0.8797	High Similarity	NPC476861
0.8797	High Similarity	NPC476853
0.8797	High Similarity	NPC472282
0.8797	High Similarity	NPC473753
0.8797	High Similarity	NPC473766
0.8792	High Similarity	NPC346
0.8792	High Similarity	NPC62799
0.879	High Similarity	NPC476860
0.8782	High Similarity	NPC117986
0.8782	High Similarity	NPC193798
0.8782	High Similarity	NPC96443
0.8782	High Similarity	NPC472668
0.8782	High Similarity	NPC188649
0.8782	High Similarity	NPC329938
0.8782	High Similarity	NPC263432
0.8782	High Similarity	NPC290400
0.8774	High Similarity	NPC474932
0.8774	High Similarity	NPC477403
0.8767	High Similarity	NPC67003
0.8766	High Similarity	NPC41880
0.8766	High Similarity	NPC263265
0.8759	High Similarity	NPC220094
0.875	High Similarity	NPC214572
0.875	High Similarity	NPC169299
0.875	High Similarity	NPC160818
0.8742	High Similarity	NPC211625
0.8734	High Similarity	NPC478178
0.8734	High Similarity	NPC23387
0.8733	High Similarity	NPC250228
0.8726	High Similarity	NPC88841
0.8726	High Similarity	NPC472669
0.8726	High Similarity	NPC288602
0.8725	High Similarity	NPC5676
0.8718	High Similarity	NPC191828
0.8718	High Similarity	NPC477402
0.8716	High Similarity	NPC470741
0.871	High Similarity	NPC187149
0.871	High Similarity	NPC195954
0.871	High Similarity	NPC472776
0.871	High Similarity	NPC472777
0.871	High Similarity	NPC472778
0.8707	High Similarity	NPC20500
0.8693	High Similarity	NPC75906
0.8693	High Similarity	NPC268905
0.8693	High Similarity	NPC44577
0.8684	High Similarity	NPC46551
0.8684	High Similarity	NPC212257
0.8679	High Similarity	NPC472651
0.8679	High Similarity	NPC100333
0.8671	High Similarity	NPC123088
0.8671	High Similarity	NPC276735
0.8662	High Similarity	NPC471167
0.8662	High Similarity	NPC472767
0.8662	High Similarity	NPC6326
0.8662	High Similarity	NPC471166
0.8654	High Similarity	NPC475226
0.8654	High Similarity	NPC262872
0.8642	High Similarity	NPC477824
0.8625	High Similarity	NPC327922
0.8625	High Similarity	NPC472652
0.8625	High Similarity	NPC296558
0.8608	High Similarity	NPC224394
0.8608	High Similarity	NPC471168
0.8608	High Similarity	NPC663
0.8591	High Similarity	NPC243577
0.859	High Similarity	NPC88007
0.8589	High Similarity	NPC262386
0.8571	High Similarity	NPC29695
0.8571	High Similarity	NPC308205
0.8571	High Similarity	NPC476940
0.8571	High Similarity	NPC302392
0.8571	High Similarity	NPC182427
0.8571	High Similarity	NPC322546
0.8571	High Similarity	NPC476939
0.8562	High Similarity	NPC270312
0.8562	High Similarity	NPC476936
0.8562	High Similarity	NPC478179
0.8562	High Similarity	NPC470742
0.8544	High Similarity	NPC68848
0.8544	High Similarity	NPC197596
0.8537	High Similarity	NPC470181
0.8533	High Similarity	NPC86935
0.8533	High Similarity	NPC84479
0.8526	High Similarity	NPC104736
0.8526	High Similarity	NPC469485
0.8523	High Similarity	NPC62103
0.8523	High Similarity	NPC20578
0.8516	High Similarity	NPC114880
0.8514	High Similarity	NPC56197
0.85	High Similarity	NPC149945

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 NPC476122 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	1027
0.2-0.3	2092
0.3-0.4	2705
0.4-0.5	1900
0.5-0.6	796
0.6-0.7	266
0.7-0.8	22
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
0.8581	High Similarity	NPD5761	Phase 2
0.8581	High Similarity	NPD5760	Phase 2
0.8118	Intermediate Similarity	NPD8434	Phase 2
0.7914	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD5494	Approved
0.7669	Intermediate Similarity	NPD7819	Suspended
0.7625	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3749	Approved
0.7375	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7411	Suspended
0.7325	Intermediate Similarity	NPD2796	Approved
0.7321	Intermediate Similarity	NPD7075	Discontinued
0.7314	Intermediate Similarity	NPD6765	Approved
0.7314	Intermediate Similarity	NPD6764	Approved
0.7314	Intermediate Similarity	NPD6559	Discontinued
0.7305	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6599	Discontinued
0.725	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4628	Phase 3
0.7241	Intermediate Similarity	NPD5844	Phase 1
0.7193	Intermediate Similarity	NPD6959	Discontinued
0.719	Intermediate Similarity	NPD6832	Phase 2
0.7188	Intermediate Similarity	NPD1243	Approved
0.7178	Intermediate Similarity	NPD2533	Approved
0.7178	Intermediate Similarity	NPD2534	Approved
0.7178	Intermediate Similarity	NPD2532	Approved
0.7176	Intermediate Similarity	NPD919	Approved
0.717	Intermediate Similarity	NPD1471	Phase 3
0.717	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3748	Approved
0.7151	Intermediate Similarity	NPD6784	Approved
0.7151	Intermediate Similarity	NPD6785	Approved
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6273	Approved
0.7108	Intermediate Similarity	NPD3226	Approved
0.7101	Intermediate Similarity	NPD5402	Approved
0.7093	Intermediate Similarity	NPD1247	Approved
0.7086	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6801	Discontinued
0.7069	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4380	Phase 2
0.7063	Intermediate Similarity	NPD2346	Discontinued
0.7059	Intermediate Similarity	NPD7768	Phase 2
0.7041	Intermediate Similarity	NPD8404	Phase 2
0.7041	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7029	Intermediate Similarity	NPD7473	Discontinued
0.7019	Intermediate Similarity	NPD1549	Phase 2
0.7018	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6799	Approved
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD6100	Approved
0.7	Intermediate Similarity	NPD3817	Phase 2
0.6994	Remote Similarity	NPD8127	Discontinued
0.6975	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6232	Discontinued
0.6949	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2799	Discontinued
0.6933	Remote Similarity	NPD3750	Approved
0.6914	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3926	Phase 2
0.691	Remote Similarity	NPD7074	Phase 3
0.6894	Remote Similarity	NPD2935	Discontinued
0.6893	Remote Similarity	NPD3818	Discontinued
0.6886	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5403	Approved
0.6882	Remote Similarity	NPD1934	Approved
0.6879	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6166	Phase 2
0.6875	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2800	Approved
0.6867	Remote Similarity	NPD5401	Approved
0.6857	Remote Similarity	NPD7229	Phase 3
0.6855	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7054	Approved
0.6848	Remote Similarity	NPD7236	Approved
0.6842	Remote Similarity	NPD1465	Phase 2
0.6835	Remote Similarity	NPD8032	Phase 2
0.6832	Remote Similarity	NPD7033	Discontinued
0.6831	Remote Similarity	NPD8150	Discontinued
0.6821	Remote Similarity	NPD17	Approved
0.6816	Remote Similarity	NPD7472	Approved
0.6805	Remote Similarity	NPD7458	Discontinued
0.6798	Remote Similarity	NPD7228	Approved
0.6796	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4307	Phase 2
0.6784	Remote Similarity	NPD37	Approved
0.6778	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2313	Discontinued
0.6771	Remote Similarity	NPD7435	Discontinued
0.6763	Remote Similarity	NPD4967	Phase 2
0.6763	Remote Similarity	NPD3882	Suspended
0.6763	Remote Similarity	NPD4966	Approved
0.6763	Remote Similarity	NPD4965	Approved
0.6761	Remote Similarity	NPD5711	Approved
0.6761	Remote Similarity	NPD6808	Phase 2
0.6761	Remote Similarity	NPD5710	Approved
0.6748	Remote Similarity	NPD2344	Approved
0.6746	Remote Similarity	NPD7239	Suspended
0.6744	Remote Similarity	NPD2801	Approved
0.674	Remote Similarity	NPD7251	Discontinued
0.6737	Remote Similarity	NPD8285	Discontinued
0.6732	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1510	Phase 2
0.6727	Remote Similarity	NPD7003	Approved
0.6726	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7799	Discontinued
0.6704	Remote Similarity	NPD3751	Discontinued
0.6703	Remote Similarity	NPD7808	Phase 3
0.6688	Remote Similarity	NPD3972	Approved
0.6688	Remote Similarity	NPD1608	Approved
0.6686	Remote Similarity	NPD6234	Discontinued
0.6685	Remote Similarity	NPD6797	Phase 2
0.6684	Remote Similarity	NPD7696	Phase 3
0.6684	Remote Similarity	NPD7697	Approved
0.6684	Remote Similarity	NPD7497	Discontinued
0.6684	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD3787	Discontinued
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7685	Pre-registration
0.6648	Remote Similarity	NPD7240	Approved
0.6647	Remote Similarity	NPD8455	Phase 2
0.6646	Remote Similarity	NPD1933	Approved
0.663	Remote Similarity	NPD8407	Phase 2
0.6628	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4308	Phase 3
0.6624	Remote Similarity	NPD1019	Discontinued
0.6616	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7783	Phase 2
0.6615	Remote Similarity	NPD6778	Approved
0.6615	Remote Similarity	NPD6780	Approved
0.6615	Remote Similarity	NPD6776	Approved
0.6615	Remote Similarity	NPD6782	Approved
0.6615	Remote Similarity	NPD6777	Approved
0.6615	Remote Similarity	NPD6781	Approved
0.6615	Remote Similarity	NPD4107	Approved
0.6615	Remote Similarity	NPD6779	Approved
0.661	Remote Similarity	NPD7199	Phase 2
0.6609	Remote Similarity	NPD5353	Approved
0.6609	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1607	Approved
0.6593	Remote Similarity	NPD5953	Discontinued
0.6587	Remote Similarity	NPD2309	Approved
0.6585	Remote Similarity	NPD2438	Suspended
0.6584	Remote Similarity	NPD2979	Phase 3
0.6584	Remote Similarity	NPD1240	Approved
0.6578	Remote Similarity	NPD4287	Approved
0.6575	Remote Similarity	NPD7286	Phase 2
0.6569	Remote Similarity	NPD7907	Approved
0.6566	Remote Similarity	NPD7874	Approved
0.6566	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7870	Phase 2
0.6564	Remote Similarity	NPD7871	Phase 2
0.6562	Remote Similarity	NPD3268	Approved
0.6561	Remote Similarity	NPD2797	Approved
0.6557	Remote Similarity	NPD8368	Discontinued
0.6548	Remote Similarity	NPD7701	Phase 2
0.6545	Remote Similarity	NPD6004	Phase 3
0.6545	Remote Similarity	NPD6005	Phase 3
0.6545	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6002	Phase 3
0.6543	Remote Similarity	NPD6355	Discontinued
0.6543	Remote Similarity	NPD5124	Phase 1
0.6543	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5585	Approved
0.6532	Remote Similarity	NPD5890	Approved
0.6532	Remote Similarity	NPD5889	Approved
0.6527	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7177	Discontinued
0.6519	Remote Similarity	NPD2798	Approved
0.6509	Remote Similarity	NPD1511	Approved
0.6503	Remote Similarity	NPD6651	Approved
0.65	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4482	Phase 3
0.6494	Remote Similarity	NPD6844	Discontinued
0.6494	Remote Similarity	NPD6279	Approved
0.6494	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6280	Approved
0.6488	Remote Similarity	NPD3887	Approved
0.6481	Remote Similarity	NPD4140	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