NPASS Compound

Structure

NPC249021 OpenBabel07101719512D 39 43 0 0 1 0 0 0 0 0999 V2000 -0.9955 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8188 -1.6600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0231 1.0284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5892 1.9294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0710 0.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3404 4.3995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2482 0.3205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9173 1.0636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4637 2.5346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2738 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 -0.7728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4392 1.7217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 0.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7198 -1.2261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3347 0.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3890 1.5374 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7366 2.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9683 0.3345 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6369 0.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3647 2.9684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -1.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 0.2272 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0259 1.1031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 0.7272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6945 1.2029 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7366 0.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1294 1.7272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5460 -1.7894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 3.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1909 2.4051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -2.2728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4113 2.6866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4394 3.9657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4173 1.9296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7945 -0.2289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -0.7728 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 15 2 0 0 0 0 2 16 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 35 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 36 1 0 0 0 0 10 18 1 0 0 0 0 10 22 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 19 1 0 0 0 0 12 26 1 0 0 0 0 13 23 1 0 0 0 0 14 17 2 0 0 0 0 14 36 1 0 0 0 0 15 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 2 0 0 0 0 16 37 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 18 27 1 6 0 0 0 19 29 1 0 0 0 0 19 31 2 0 0 0 0 20 25 1 0 0 0 0 20 37 1 1 0 0 0 21 27 1 1 0 0 0 21 39 1 0 0 0 0 22 32 2 0 0 0 0 22 35 1 0 0 0 0 23 33 2 0 0 0 0 23 38 1 0 0 0 0 24 26 1 6 0 0 0 24 38 1 0 0 0 0 26 28 1 6 0 0 0 27 29 1 1 0 0 0 28 13 1 6 0 0 0 28 39 1 0 0 0 0 29 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.23
Volume:	536.805
LogP:	3.186
LogD:	2.115
LogS:	-4.864
# Rotatable Bonds:	6
TPSA:	138.57
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.341
Synthetic Accessibility Score:	6.453
Fsp3:	0.655
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:	-5.345
MDCK Permeability:	7.282297883648425e-05
Pgp-inhibitor:	0.973
Pgp-substrate:	0.541
Human Intestinal Absorption (HIA):	0.614
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.945
Plasma Protein Binding (PPB):	63.99628448486328%
Volume Distribution (VD):	0.617
Pgp-substrate:	39.30729675292969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.297
CYP2C9-inhibitor:	0.358
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.748
CYP3A4-substrate:	0.77

ADMET: Excretion

Clearance (CL):	5.825
Half-life (T1/2):	0.374

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.489
Drug-inuced Liver Injury (DILI):	0.648
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.255
Carcinogencity:	0.894
Eye Corrosion:	0.317
Eye Irritation:	0.091
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC249021

Natural Product ID:	NPC249021
*Common Name:**	Cineracipadesin C
IUPAC Name:	n.a.
Synonyms:	Cineracipadesin C
Standard InCHIKey:	ASBTXKZKJYWTLW-DYOGWWOHSA-N
Standard InCHI:	InChI=1S/C29H36O10/c1-15-28-13-23(33)38-24(17-8-9-36-14-17)26(28,5)12-19(31)29(15,34)27(6)18(10-22(32)35-7)25(3,4)20(37-16(2)30)11-21(27)39-28/h8-9,14,18,20-21,24,34H,1,10-13H2,2-7H3/t18-,20+,21-,24-,26-,27+,28-,29-/m0/s1
SMILES:	COC(=O)C[C@H]1C(C)(C)[C@H](OC(=O)C)C[C@H]2[C@]1(C)[C@@]1(O)C(=O)C[C@@]3([C@@](O2)(C1=C)CC(=O)O[C@H]3c1ccoc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560366
PubChem CID:	42639820
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic 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[502963]

☑ 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 NPC249021 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	352
0.1-0.2	1429
0.2-0.3	3088
0.3-0.4	5355
0.4-0.5	10054
0.5-0.6	10041
0.6-0.7	8450
0.7-0.8	3461
0.8-0.85	282
0.85-0.9	122
0.9-0.95	60
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9801	High Similarity	NPC82851
0.9797	High Similarity	NPC282445
0.9481	High Similarity	NPC477405
0.9467	High Similarity	NPC469503
0.9463	High Similarity	NPC476122
0.9419	High Similarity	NPC470940
0.9416	High Similarity	NPC200782
0.9355	High Similarity	NPC292389
0.9355	High Similarity	NPC39986
0.9355	High Similarity	NPC469338
0.9355	High Similarity	NPC134254
0.9355	High Similarity	NPC302369
0.9346	High Similarity	NPC472772
0.9342	High Similarity	NPC469336
0.9338	High Similarity	NPC476201
0.9333	High Similarity	NPC477404
0.9333	High Similarity	NPC196864
0.9299	High Similarity	NPC173516
0.9295	High Similarity	NPC470182
0.9295	High Similarity	NPC469849
0.9295	High Similarity	NPC276551
0.929	High Similarity	NPC193798
0.929	High Similarity	NPC69028
0.929	High Similarity	NPC329938
0.929	High Similarity	NPC5079
0.9286	High Similarity	NPC477403
0.9276	High Similarity	NPC30222
0.9276	High Similarity	NPC178932
0.9241	High Similarity	NPC160651
0.9241	High Similarity	NPC471397
0.9236	High Similarity	NPC470875
0.9231	High Similarity	NPC234660
0.9231	High Similarity	NPC51568
0.9226	High Similarity	NPC472653
0.9226	High Similarity	NPC25255
0.9226	High Similarity	NPC477402
0.9226	High Similarity	NPC335761
0.9221	High Similarity	NPC36655
0.9221	High Similarity	NPC45101
0.9221	High Similarity	NPC261597
0.9221	High Similarity	NPC286722
0.9216	High Similarity	NPC35000
0.9216	High Similarity	NPC476262
0.9205	High Similarity	NPC159927
0.9205	High Similarity	NPC469335
0.9177	High Similarity	NPC472774
0.9177	High Similarity	NPC472775
0.9177	High Similarity	NPC472282
0.9172	High Similarity	NPC476856
0.9172	High Similarity	NPC476858
0.9172	High Similarity	NPC476857
0.9172	High Similarity	NPC271657
0.9167	High Similarity	NPC18347
0.9167	High Similarity	NPC117986
0.9167	High Similarity	NPC149896
0.9167	High Similarity	NPC263432
0.9167	High Similarity	NPC472771
0.9167	High Similarity	NPC470939
0.9161	High Similarity	NPC473473
0.9161	High Similarity	NPC475295
0.9161	High Similarity	NPC475967
0.9156	High Similarity	NPC209364
0.9156	High Similarity	NPC107646
0.9133	High Similarity	NPC470941
0.9119	High Similarity	NPC271235
0.9108	High Similarity	NPC663
0.9108	High Similarity	NPC419
0.9108	High Similarity	NPC224394
0.9108	High Similarity	NPC472773
0.9103	High Similarity	NPC475381
0.9097	High Similarity	NPC472283
0.9091	High Similarity	NPC469850
0.9091	High Similarity	NPC214541
0.9091	High Similarity	NPC44675
0.9091	High Similarity	NPC264943
0.9085	High Similarity	NPC44577
0.9062	High Similarity	NPC82602
0.906	High Similarity	NPC476944
0.9057	High Similarity	NPC476861
0.9057	High Similarity	NPC476850
0.9057	High Similarity	NPC476853
0.9051	High Similarity	NPC123088
0.9051	High Similarity	NPC476860
0.9045	High Similarity	NPC207978
0.9045	High Similarity	NPC290400
0.9045	High Similarity	NPC96443
0.9038	High Similarity	NPC474611
0.9032	High Similarity	NPC469485
0.9032	High Similarity	NPC126723
0.9006	High Similarity	NPC169299
0.9006	High Similarity	NPC160818
0.8994	High Similarity	NPC149945
0.8994	High Similarity	NPC93172
0.8994	High Similarity	NPC97574
0.8994	High Similarity	NPC478178
0.8994	High Similarity	NPC23387
0.8993	High Similarity	NPC243577
0.8987	High Similarity	NPC198047
0.8987	High Similarity	NPC88841
0.8987	High Similarity	NPC165218
0.8987	High Similarity	NPC288602
0.8987	High Similarity	NPC469846
0.8981	High Similarity	NPC305016
0.8974	High Similarity	NPC173544
0.8974	High Similarity	NPC187149
0.8974	High Similarity	NPC167142
0.8974	High Similarity	NPC299038
0.894	High Similarity	NPC346
0.894	High Similarity	NPC262198
0.8938	High Similarity	NPC472651
0.8926	High Similarity	NPC121158
0.8924	High Similarity	NPC211777
0.8924	High Similarity	NPC188649
0.8917	High Similarity	NPC237155
0.8917	High Similarity	NPC307383
0.891	High Similarity	NPC60973
0.891	High Similarity	NPC41880
0.8903	High Similarity	NPC57998
0.8889	High Similarity	NPC211625
0.8889	High Similarity	NPC195325
0.8889	High Similarity	NPC472654
0.8882	High Similarity	NPC472652
0.8882	High Similarity	NPC250228
0.8882	High Similarity	NPC296558
0.8882	High Similarity	NPC221809
0.8882	High Similarity	NPC255414
0.8874	High Similarity	NPC41182
0.8868	High Similarity	NPC476197
0.8846	High Similarity	NPC281258
0.8839	High Similarity	NPC75906
0.8831	High Similarity	NPC212257
0.8831	High Similarity	NPC156189
0.882	High Similarity	NPC473766
0.882	High Similarity	NPC478179
0.882	High Similarity	NPC473753
0.8808	High Similarity	NPC251865
0.8805	High Similarity	NPC472767
0.8797	High Similarity	NPC262872
0.879	High Similarity	NPC263265
0.8788	High Similarity	NPC478177
0.8784	High Similarity	NPC476943
0.8782	High Similarity	NPC114880
0.878	High Similarity	NPC236004
0.878	High Similarity	NPC94763
0.878	High Similarity	NPC471437
0.8774	High Similarity	NPC18135
0.8766	High Similarity	NPC125182
0.8766	High Similarity	NPC69647
0.8758	High Similarity	NPC475779
0.8758	High Similarity	NPC472141
0.8758	High Similarity	NPC214600
0.875	High Similarity	NPC472139
0.8742	High Similarity	NPC191828
0.8742	High Similarity	NPC470789
0.8734	High Similarity	NPC195954
0.8734	High Similarity	NPC472778
0.8734	High Similarity	NPC88007
0.8734	High Similarity	NPC472777
0.8734	High Similarity	NPC472776
0.8727	High Similarity	NPC262386
0.8726	High Similarity	NPC75310
0.8718	High Similarity	NPC246164
0.8712	High Similarity	NPC470995
0.871	High Similarity	NPC46551
0.8704	High Similarity	NPC100333
0.8688	High Similarity	NPC68848
0.8688	High Similarity	NPC6326
0.8684	High Similarity	NPC142113
0.8679	High Similarity	NPC475226
0.8675	High Similarity	NPC20578
0.8675	High Similarity	NPC472665
0.8675	High Similarity	NPC62103
0.8671	High Similarity	NPC204663
0.8671	High Similarity	NPC104736
0.8667	High Similarity	NPC67003
0.8654	High Similarity	NPC272590
0.8649	High Similarity	NPC46896
0.8645	High Similarity	NPC470790
0.8645	High Similarity	NPC470791
0.8642	High Similarity	NPC121995
0.8636	High Similarity	NPC216755
0.8636	High Similarity	NPC471174
0.8627	High Similarity	NPC5676
0.8618	High Similarity	NPC476946
0.8616	High Similarity	NPC470118
0.8616	High Similarity	NPC194499
0.8616	High Similarity	NPC81405
0.8616	High Similarity	NPC195131
0.8616	High Similarity	NPC304692
0.8599	High Similarity	NPC475777
0.8599	High Similarity	NPC268905
0.8599	High Similarity	NPC476940
0.8599	High Similarity	NPC476939
0.8598	High Similarity	NPC302392
0.8591	High Similarity	NPC310830
0.8589	High Similarity	NPC270312
0.8589	High Similarity	NPC472764
0.8581	High Similarity	NPC19747
0.858	High Similarity	NPC146991
0.858	High Similarity	NPC472664

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 NPC249021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	1026
0.2-0.3	2067
0.3-0.4	2609
0.4-0.5	1935
0.5-0.6	882
0.6-0.7	282
0.7-0.8	47
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8726	High Similarity	NPD5761	Phase 2
0.8726	High Similarity	NPD5760	Phase 2
0.8471	Intermediate Similarity	NPD8434	Phase 2
0.7952	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7819	Suspended
0.7784	Intermediate Similarity	NPD7075	Discontinued
0.7711	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3749	Approved
0.7657	Intermediate Similarity	NPD6764	Approved
0.7657	Intermediate Similarity	NPD6765	Approved
0.759	Intermediate Similarity	NPD7411	Suspended
0.756	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6559	Discontinued
0.753	Intermediate Similarity	NPD6599	Discontinued
0.7486	Intermediate Similarity	NPD6784	Approved
0.7486	Intermediate Similarity	NPD6785	Approved
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5494	Approved
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD920	Approved
0.7442	Intermediate Similarity	NPD6959	Discontinued
0.744	Intermediate Similarity	NPD6801	Discontinued
0.7439	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4628	Phase 3
0.7386	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3226	Approved
0.7353	Intermediate Similarity	NPD5402	Approved
0.7347	Intermediate Similarity	NPD8404	Phase 2
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD2534	Approved
0.7333	Intermediate Similarity	NPD2533	Approved
0.7329	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4380	Phase 2
0.7314	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6166	Phase 2
0.7314	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5844	Phase 1
0.7284	Intermediate Similarity	NPD1549	Phase 2
0.7278	Intermediate Similarity	NPD8313	Approved
0.7278	Intermediate Similarity	NPD8312	Approved
0.7273	Intermediate Similarity	NPD7473	Discontinued
0.7273	Intermediate Similarity	NPD6799	Approved
0.7267	Intermediate Similarity	NPD6100	Approved
0.7267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6099	Approved
0.7251	Intermediate Similarity	NPD3817	Phase 2
0.7246	Intermediate Similarity	NPD5403	Approved
0.7239	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD919	Approved
0.7222	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2346	Discontinued
0.7222	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1471	Phase 3
0.7212	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7236	Approved
0.7209	Intermediate Similarity	NPD7768	Phase 2
0.7209	Intermediate Similarity	NPD3882	Suspended
0.7207	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3750	Approved
0.7186	Intermediate Similarity	NPD6273	Approved
0.7167	Intermediate Similarity	NPD7251	Discontinued
0.716	Intermediate Similarity	NPD2796	Approved
0.716	Intermediate Similarity	NPD1551	Phase 2
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7151	Intermediate Similarity	NPD7074	Phase 3
0.7135	Intermediate Similarity	NPD1934	Approved
0.7135	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD2800	Approved
0.7127	Intermediate Similarity	NPD7808	Phase 3
0.7127	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5401	Approved
0.7111	Intermediate Similarity	NPD6797	Phase 2
0.7102	Intermediate Similarity	NPD6232	Discontinued
0.7101	Intermediate Similarity	NPD7239	Suspended
0.7099	Intermediate Similarity	NPD2799	Discontinued
0.7095	Intermediate Similarity	NPD7054	Approved
0.7083	Intermediate Similarity	NPD7435	Discontinued
0.7073	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7458	Discontinued
0.7056	Intermediate Similarity	NPD7472	Approved
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.7045	Intermediate Similarity	NPD1247	Approved
0.7039	Intermediate Similarity	NPD3751	Discontinued
0.7039	Intermediate Similarity	NPD7799	Discontinued
0.703	Intermediate Similarity	NPD1243	Approved
0.7012	Intermediate Similarity	NPD2344	Approved
0.6995	Remote Similarity	NPD7696	Phase 3
0.6995	Remote Similarity	NPD7698	Approved
0.6995	Remote Similarity	NPD7697	Approved
0.6994	Remote Similarity	NPD1465	Phase 2
0.6994	Remote Similarity	NPD1510	Phase 2
0.6994	Remote Similarity	NPD3748	Approved
0.6994	Remote Similarity	NPD7033	Discontinued
0.6966	Remote Similarity	NPD3926	Phase 2
0.6951	Remote Similarity	NPD2935	Discontinued
0.6944	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7228	Approved
0.6937	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2313	Discontinued
0.6936	Remote Similarity	NPD37	Approved
0.6927	Remote Similarity	NPD6779	Approved
0.6927	Remote Similarity	NPD6777	Approved
0.6927	Remote Similarity	NPD6776	Approved
0.6927	Remote Similarity	NPD6781	Approved
0.6927	Remote Similarity	NPD6778	Approved
0.6927	Remote Similarity	NPD6782	Approved
0.6927	Remote Similarity	NPD6780	Approved
0.6918	Remote Similarity	NPD6832	Phase 2
0.6914	Remote Similarity	NPD4966	Approved
0.6914	Remote Similarity	NPD4965	Approved
0.6914	Remote Similarity	NPD4967	Phase 2
0.691	Remote Similarity	NPD5711	Approved
0.691	Remote Similarity	NPD5710	Approved
0.691	Remote Similarity	NPD3787	Discontinued
0.691	Remote Similarity	NPD7229	Phase 3
0.6897	Remote Similarity	NPD2801	Approved
0.6886	Remote Similarity	NPD7003	Approved
0.6882	Remote Similarity	NPD1512	Approved
0.6872	Remote Similarity	NPD7871	Phase 2
0.6872	Remote Similarity	NPD8320	Phase 1
0.6872	Remote Similarity	NPD8319	Approved
0.6872	Remote Similarity	NPD7870	Phase 2
0.6871	Remote Similarity	NPD1607	Approved
0.6869	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7874	Approved
0.6865	Remote Similarity	NPD8407	Phase 2
0.6863	Remote Similarity	NPD7907	Approved
0.6853	Remote Similarity	NPD7701	Phase 2
0.6852	Remote Similarity	NPD1240	Approved
0.6845	Remote Similarity	NPD2309	Approved
0.6836	Remote Similarity	NPD6234	Discontinued
0.6832	Remote Similarity	NPD3268	Approved
0.6832	Remote Similarity	NPD3764	Approved
0.6831	Remote Similarity	NPD5953	Discontinued
0.6813	Remote Similarity	NPD7286	Phase 2
0.681	Remote Similarity	NPD6355	Discontinued
0.6809	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4287	Approved
0.6796	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD8368	Discontinued
0.6793	Remote Similarity	NPD7685	Pre-registration
0.6788	Remote Similarity	NPD4308	Phase 3
0.6786	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6651	Approved
0.6765	Remote Similarity	NPD1511	Approved
0.6765	Remote Similarity	NPD4665	Approved
0.6765	Remote Similarity	NPD4111	Phase 1
0.6752	Remote Similarity	NPD1608	Approved
0.675	Remote Similarity	NPD7801	Approved
0.6744	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7699	Phase 2
0.6736	Remote Similarity	NPD7700	Phase 2
0.673	Remote Similarity	NPD2797	Approved
0.6727	Remote Similarity	NPD7097	Phase 1
0.6723	Remote Similarity	NPD7057	Phase 3
0.6723	Remote Similarity	NPD7058	Phase 2
0.672	Remote Similarity	NPD8361	Approved
0.672	Remote Similarity	NPD8360	Approved
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5124	Phase 1
0.6705	Remote Similarity	NPD8455	Phase 2
0.6703	Remote Similarity	NPD7240	Approved
0.6687	Remote Similarity	NPD8032	Phase 2
0.6684	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD7199	Phase 2
0.665	Remote Similarity	NPD7497	Discontinued
0.665	Remote Similarity	NPD8151	Discontinued
0.6647	Remote Similarity	NPD6190	Approved
0.6646	Remote Similarity	NPD9717	Approved
0.6632	Remote Similarity	NPD8435	Approved
0.663	Remote Similarity	NPD6808	Phase 2
0.6626	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1203	Approved
0.6615	Remote Similarity	NPD8285	Discontinued
0.6607	Remote Similarity	NPD5763	Approved
0.6607	Remote Similarity	NPD5762	Approved
0.6606	Remote Similarity	NPD447	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