NPASS Compound

Structure

NPC469849 OpenBabel07101719252D 41 45 0 0 1 0 0 0 0 0999 V2000 3.8414 2.0294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3577 -0.5717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0075 2.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5075 1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5560 2.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6632 2.8232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9905 1.0406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0196 2.7160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2086 0.4171 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 1.7272 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9505 3.0814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2778 0.7824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 0.5243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5075 1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0995 4.0702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1287 1.7713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2819 -0.9594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7323 2.4579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 0.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4959 0.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 17 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 7 38 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 30 1 0 0 0 0 12 39 1 0 0 0 0 13 21 1 0 0 0 0 13 24 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 32 1 0 0 0 0 16 18 2 0 0 0 0 16 39 1 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 31 1 6 0 0 0 21 30 1 0 0 0 0 22 29 1 0 0 0 0 22 31 1 1 0 0 0 23 33 2 0 0 0 0 23 38 1 0 0 0 0 24 34 2 0 0 0 0 24 40 1 0 0 0 0 25 30 1 1 0 0 0 25 40 1 0 0 0 0 26 35 2 0 0 0 0 26 41 1 0 0 0 0 27 31 1 0 0 0 0 27 32 1 0 0 0 0 27 36 2 0 0 0 0 28 29 1 0 0 0 0 28 32 1 6 0 0 0 28 41 1 0 0 0 0 30 5 1 1 0 0 0 31 6 1 1 0 0 0 32 37 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.28
Volume:	579.903
LogP:	4.323
LogD:	3.292
LogS:	-5.263
# Rotatable Bonds:	8
TPSA:	129.34
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	6.037
Fsp3:	0.688
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:	-4.95
MDCK Permeability:	2.9089422241668217e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.287
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	83.17036437988281%
Volume Distribution (VD):	1.573
Pgp-substrate:	9.93759536743164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.141
CYP2C19-inhibitor:	0.601
CYP2C19-substrate:	0.429
CYP2C9-inhibitor:	0.886
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.723

ADMET: Excretion

Clearance (CL):	4.503
Half-life (T1/2):	0.272

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.347
Drug-inuced Liver Injury (DILI):	0.781
AMES Toxicity:	0.311
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.343
Carcinogencity:	0.5
Eye Corrosion:	0.033
Eye Irritation:	0.117
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: NPC469849

Natural Product ID:	NPC469849
*Common Name:**	Cipadesin N
IUPAC Name:	n.a.
Synonyms:	Cipadesin N
Standard InCHIKey:	WDFITJJRJNQVKR-MHRNCSRTSA-N
Standard InCHI:	InChI=1S/C32H42O9/c1-8-17(2)26(35)41-28-29(3,4)22(14-23(33)38-7)31(6)20-9-11-30(5)21(19(20)15-32(28,37)27(31)36)13-24(34)40-25(30)18-10-12-39-16-18/h10,12,16-17,20,22,25,28,37H,8-9,11,13-15H2,1-7H3/t17?,20-,22-,25-,28-,30+,31+,32-/m0/s1
SMILES:	CCC(C)C(=O)OC1C(C(C2(C3CCC4(C(OC(=O)CC4=C3CC1(C2=O)O)C5=COC=C5)C)C)CC(=O)OC)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215111
PubChem CID:	46918645
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO14263	Cipadessa baccifera	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20666364]
NPO14263	Cipadessa baccifera	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32468815]
NPO14263	Cipadessa baccifera	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14263	Cipadessa baccifera	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14263	Cipadessa baccifera	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14263	Cipadessa baccifera	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[530059]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[530059]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[530059]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[530059]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[530059]

☑ 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 NPC469849 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	356
0.1-0.2	1413
0.2-0.3	3106
0.3-0.4	5361
0.4-0.5	9821
0.5-0.6	9963
0.6-0.7	8543
0.7-0.8	3581
0.8-0.85	312
0.85-0.9	140
0.9-0.95	90
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC292389
0.9935	High Similarity	NPC469338
0.9935	High Similarity	NPC470875
0.987	High Similarity	NPC470940
0.987	High Similarity	NPC276551
0.9744	High Similarity	NPC173516
0.974	High Similarity	NPC69028
0.9682	High Similarity	NPC471397
0.9682	High Similarity	NPC160651
0.9677	High Similarity	NPC477405
0.9618	High Similarity	NPC472282
0.9613	High Similarity	NPC329938
0.9548	High Similarity	NPC477402
0.9545	High Similarity	NPC472283
0.9542	High Similarity	NPC264943
0.9494	High Similarity	NPC472774
0.9494	High Similarity	NPC472775
0.9487	High Similarity	NPC82851
0.9487	High Similarity	NPC263432
0.9484	High Similarity	NPC477403
0.9427	High Similarity	NPC472773
0.9423	High Similarity	NPC472653
0.9423	High Similarity	NPC25255
0.9419	High Similarity	NPC173544
0.9416	High Similarity	NPC469336
0.9367	High Similarity	NPC476858
0.9367	High Similarity	NPC476856
0.9367	High Similarity	NPC476857
0.9363	High Similarity	NPC5079
0.9363	High Similarity	NPC193798
0.9363	High Similarity	NPC472771
0.9355	High Similarity	NPC469485
0.9351	High Similarity	NPC178932
0.9304	High Similarity	NPC51568
0.9304	High Similarity	NPC234660
0.9295	High Similarity	NPC249021
0.9295	High Similarity	NPC286722
0.9295	High Similarity	NPC167142
0.929	High Similarity	NPC469850
0.929	High Similarity	NPC44675
0.929	High Similarity	NPC281258
0.929	High Similarity	NPC214541
0.9281	High Similarity	NPC159927
0.9281	High Similarity	NPC469335
0.925	High Similarity	NPC476853
0.925	High Similarity	NPC476850
0.925	High Similarity	NPC476861
0.9245	High Similarity	NPC123088
0.9245	High Similarity	NPC470182
0.9245	High Similarity	NPC476860
0.9241	High Similarity	NPC470939
0.9241	High Similarity	NPC200782
0.9241	High Similarity	NPC149896
0.9236	High Similarity	NPC475967
0.9236	High Similarity	NPC473473
0.9236	High Similarity	NPC475295
0.9231	High Similarity	NPC60973
0.9231	High Similarity	NPC209364
0.9193	High Similarity	NPC271235
0.9193	High Similarity	NPC472652
0.9187	High Similarity	NPC475779
0.9187	High Similarity	NPC23387
0.9182	High Similarity	NPC134254
0.9182	High Similarity	NPC476197
0.9182	High Similarity	NPC39986
0.9182	High Similarity	NPC302369
0.9177	High Similarity	NPC335761
0.9172	High Similarity	NPC261597
0.9172	High Similarity	NPC472772
0.9172	High Similarity	NPC36655
0.9172	High Similarity	NPC45101
0.9167	High Similarity	NPC476262
0.9161	High Similarity	NPC476201
0.9161	High Similarity	NPC469503
0.9156	High Similarity	NPC477404
0.9156	High Similarity	NPC196864
0.9136	High Similarity	NPC82602
0.913	High Similarity	NPC472651
0.913	High Similarity	NPC473753
0.913	High Similarity	NPC473766
0.9125	High Similarity	NPC271657
0.9119	High Similarity	NPC96443
0.9119	High Similarity	NPC290400
0.9119	High Similarity	NPC18347
0.9114	High Similarity	NPC307383
0.9114	High Similarity	NPC237155
0.9108	High Similarity	NPC107646
0.9103	High Similarity	NPC282445
0.9091	High Similarity	NPC478177
0.9085	High Similarity	NPC94763
0.9062	High Similarity	NPC469846
0.9062	High Similarity	NPC663
0.9062	High Similarity	NPC224394
0.9057	High Similarity	NPC191828
0.9057	High Similarity	NPC305016
0.9057	High Similarity	NPC475381
0.9051	High Similarity	NPC187149
0.9051	High Similarity	NPC299038
0.9038	High Similarity	NPC44577
0.9032	High Similarity	NPC46551
0.9	High Similarity	NPC207978
0.9	High Similarity	NPC117986
0.9	High Similarity	NPC188649
0.9	High Similarity	NPC211777
0.8987	High Similarity	NPC126723
0.8987	High Similarity	NPC263265
0.8981	High Similarity	NPC30222
0.897	High Similarity	NPC236004
0.8963	High Similarity	NPC160818
0.8963	High Similarity	NPC169299
0.8951	High Similarity	NPC472141
0.8951	High Similarity	NPC121995
0.8951	High Similarity	NPC93172
0.8951	High Similarity	NPC97574
0.8944	High Similarity	NPC472139
0.8944	High Similarity	NPC419
0.8944	High Similarity	NPC88841
0.8944	High Similarity	NPC198047
0.8944	High Similarity	NPC288602
0.8938	High Similarity	NPC470789
0.8938	High Similarity	NPC287559
0.8931	High Similarity	NPC472778
0.8931	High Similarity	NPC472776
0.8931	High Similarity	NPC472777
0.8924	High Similarity	NPC92979
0.8924	High Similarity	NPC35000
0.891	High Similarity	NPC476122
0.8896	High Similarity	NPC100333
0.8896	High Similarity	NPC262198
0.8882	High Similarity	NPC18986
0.8882	High Similarity	NPC68848
0.8875	High Similarity	NPC262872
0.8855	High Similarity	NPC471437
0.8854	High Similarity	NPC18135
0.8848	High Similarity	NPC285227
0.8846	High Similarity	NPC125182
0.8846	High Similarity	NPC69647
0.8841	High Similarity	NPC472766
0.8841	High Similarity	NPC296558
0.8841	High Similarity	NPC472765
0.8839	High Similarity	NPC255414
0.8834	High Similarity	NPC478178
0.8824	High Similarity	NPC247563
0.8824	High Similarity	NPC242068
0.8812	High Similarity	NPC88007
0.8812	High Similarity	NPC197137
0.8802	High Similarity	NPC262386
0.8802	High Similarity	NPC469633
0.8797	High Similarity	NPC75906
0.8788	High Similarity	NPC302392
0.8788	High Similarity	NPC470995
0.878	High Similarity	NPC270312
0.878	High Similarity	NPC472764
0.878	High Similarity	NPC476224
0.8766	High Similarity	NPC142113
0.8758	High Similarity	NPC475226
0.8758	High Similarity	NPC473368
0.875	High Similarity	NPC472665
0.8743	High Similarity	NPC469576
0.8743	High Similarity	NPC471632
0.8742	High Similarity	NPC57998
0.8734	High Similarity	NPC272590
0.8727	High Similarity	NPC327922
0.872	High Similarity	NPC149945
0.8718	High Similarity	NPC470941
0.8713	High Similarity	NPC105395
0.8712	High Similarity	NPC165218
0.8712	High Similarity	NPC285567
0.8696	High Similarity	NPC470118
0.8696	High Similarity	NPC194499
0.8696	High Similarity	NPC195954
0.8688	High Similarity	NPC141538
0.8688	High Similarity	NPC296807
0.8688	High Similarity	NPC155939
0.8683	High Similarity	NPC469848
0.8679	High Similarity	NPC33938
0.8679	High Similarity	NPC268905
0.8671	High Similarity	NPC470997
0.8667	High Similarity	NPC478179
0.8659	High Similarity	NPC56358
0.8659	High Similarity	NPC146991
0.8654	High Similarity	NPC346
0.865	High Similarity	NPC471166
0.865	High Similarity	NPC472767
0.865	High Similarity	NPC471167
0.865	High Similarity	NPC470792
0.865	High Similarity	NPC197596
0.8647	High Similarity	NPC470938
0.8645	High Similarity	NPC137295
0.8645	High Similarity	NPC476944
0.8642	High Similarity	NPC474611
0.8636	High Similarity	NPC121158
0.8634	High Similarity	NPC41880
0.8627	High Similarity	NPC90296
0.8625	High Similarity	NPC302054
0.8625	High Similarity	NPC253201
0.8623	High Similarity	NPC159232
0.8616	High Similarity	NPC116717
0.8608	High Similarity	NPC472654
0.8608	High Similarity	NPC234494

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 NPC469849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	1007
0.2-0.3	2140
0.3-0.4	2619
0.4-0.5	1835
0.5-0.6	911
0.6-0.7	275
0.7-0.8	56
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8765	High Similarity	NPD8434	Phase 2
0.8344	Intermediate Similarity	NPD5761	Phase 2
0.8344	Intermediate Similarity	NPD5760	Phase 2
0.8253	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6764	Approved
0.7841	Intermediate Similarity	NPD6765	Approved
0.7692	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6785	Approved
0.7667	Intermediate Similarity	NPD6784	Approved
0.7661	Intermediate Similarity	NPD7075	Discontinued
0.7588	Intermediate Similarity	NPD7819	Suspended
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7513	Intermediate Similarity	NPD8404	Phase 2
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6559	Discontinued
0.7442	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD8150	Discontinued
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7371	Intermediate Similarity	NPD5494	Approved
0.7368	Intermediate Similarity	NPD7411	Suspended
0.7341	Intermediate Similarity	NPD3817	Phase 2
0.7326	Intermediate Similarity	NPD6801	Discontinued
0.7299	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8312	Approved
0.7268	Intermediate Similarity	NPD8313	Approved
0.7262	Intermediate Similarity	NPD6799	Approved
0.7257	Intermediate Similarity	NPD3749	Approved
0.7251	Intermediate Similarity	NPD3226	Approved
0.7241	Intermediate Similarity	NPD5402	Approved
0.7232	Intermediate Similarity	NPD8127	Discontinued
0.7232	Intermediate Similarity	NPD1247	Approved
0.7222	Intermediate Similarity	NPD7799	Discontinued
0.7216	Intermediate Similarity	NPD919	Approved
0.7212	Intermediate Similarity	NPD1471	Phase 3
0.7209	Intermediate Similarity	NPD4380	Phase 2
0.7207	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6166	Phase 2
0.7207	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3882	Suspended
0.7198	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5844	Phase 1
0.7167	Intermediate Similarity	NPD7473	Discontinued
0.7159	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD920	Approved
0.7135	Intermediate Similarity	NPD8407	Phase 2
0.7135	Intermediate Similarity	NPD5403	Approved
0.7127	Intermediate Similarity	NPD3818	Discontinued
0.7127	Intermediate Similarity	NPD3751	Discontinued
0.7126	Intermediate Similarity	NPD1934	Approved
0.7126	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7808	Phase 3
0.712	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5401	Approved
0.7118	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7236	Approved
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8368	Discontinued
0.7065	Intermediate Similarity	NPD7251	Discontinued
0.7049	Intermediate Similarity	NPD7074	Phase 3
0.7033	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7907	Approved
0.7018	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6797	Phase 2
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD3787	Discontinued
0.6995	Remote Similarity	NPD7054	Approved
0.6994	Remote Similarity	NPD7239	Suspended
0.699	Remote Similarity	NPD7435	Discontinued
0.6977	Remote Similarity	NPD6273	Approved
0.6973	Remote Similarity	NPD7685	Pre-registration
0.6961	Remote Similarity	NPD3926	Phase 2
0.6957	Remote Similarity	NPD7472	Approved
0.6954	Remote Similarity	NPD7458	Discontinued
0.6944	Remote Similarity	NPD6959	Discontinued
0.6919	Remote Similarity	NPD2532	Approved
0.6919	Remote Similarity	NPD2533	Approved
0.6919	Remote Similarity	NPD2534	Approved
0.691	Remote Similarity	NPD7768	Phase 2
0.6909	Remote Similarity	NPD6355	Discontinued
0.6901	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8435	Approved
0.6895	Remote Similarity	NPD8360	Approved
0.6895	Remote Similarity	NPD8361	Approved
0.6893	Remote Similarity	NPD2801	Approved
0.6893	Remote Similarity	NPD1465	Phase 2
0.6886	Remote Similarity	NPD2799	Discontinued
0.6882	Remote Similarity	NPD3750	Approved
0.6875	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8285	Discontinued
0.6868	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7874	Approved
0.6864	Remote Similarity	NPD1549	Phase 2
0.6857	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7228	Approved
0.6845	Remote Similarity	NPD2796	Approved
0.6845	Remote Similarity	NPD6099	Approved
0.6845	Remote Similarity	NPD6100	Approved
0.6845	Remote Similarity	NPD4111	Phase 1
0.6845	Remote Similarity	NPD4665	Approved
0.6837	Remote Similarity	NPD6781	Approved
0.6837	Remote Similarity	NPD6782	Approved
0.6837	Remote Similarity	NPD4107	Approved
0.6837	Remote Similarity	NPD6778	Approved
0.6837	Remote Similarity	NPD6777	Approved
0.6837	Remote Similarity	NPD6776	Approved
0.6837	Remote Similarity	NPD6780	Approved
0.6837	Remote Similarity	NPD6779	Approved
0.6836	Remote Similarity	NPD37	Approved
0.6833	Remote Similarity	NPD6234	Discontinued
0.6824	Remote Similarity	NPD2800	Approved
0.6821	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7696	Phase 3
0.6818	Remote Similarity	NPD7697	Approved
0.6818	Remote Similarity	NPD7698	Approved
0.6816	Remote Similarity	NPD4966	Approved
0.6816	Remote Similarity	NPD4965	Approved
0.6816	Remote Similarity	NPD4967	Phase 2
0.6811	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8455	Phase 2
0.6789	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3748	Approved
0.6784	Remote Similarity	NPD8166	Discontinued
0.6784	Remote Similarity	NPD7871	Phase 2
0.6784	Remote Similarity	NPD7870	Phase 2
0.6784	Remote Similarity	NPD8320	Phase 1
0.6784	Remote Similarity	NPD8319	Approved
0.6782	Remote Similarity	NPD1512	Approved
0.6768	Remote Similarity	NPD3057	Approved
0.6766	Remote Similarity	NPD7701	Phase 2
0.6758	Remote Similarity	NPD7199	Phase 2
0.6749	Remote Similarity	NPD7801	Approved
0.6746	Remote Similarity	NPD1551	Phase 2
0.6743	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2403	Approved
0.6734	Remote Similarity	NPD7497	Discontinued
0.6727	Remote Similarity	NPD3268	Approved
0.6727	Remote Similarity	NPD2313	Discontinued
0.6726	Remote Similarity	NPD7097	Phase 1
0.6725	Remote Similarity	NPD1243	Approved
0.6717	Remote Similarity	NPD4482	Phase 3
0.6707	Remote Similarity	NPD6832	Phase 2
0.6706	Remote Similarity	NPD2344	Approved
0.6706	Remote Similarity	NPD5762	Approved
0.6706	Remote Similarity	NPD5763	Approved
0.6702	Remote Similarity	NPD7240	Approved
0.6686	Remote Similarity	NPD7033	Discontinued
0.6684	Remote Similarity	NPD8485	Approved
0.6684	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3533	Approved
0.6683	Remote Similarity	NPD2972	Approved
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7699	Phase 2
0.665	Remote Similarity	NPD8151	Discontinued
0.665	Remote Similarity	NPD7700	Phase 2
0.6647	Remote Similarity	NPD6190	Approved
0.6647	Remote Similarity	NPD2935	Discontinued
0.663	Remote Similarity	NPD7229	Phase 3
0.663	Remote Similarity	NPD7058	Phase 2
0.663	Remote Similarity	NPD7057	Phase 3
0.663	Remote Similarity	NPD6808	Phase 2
0.6627	Remote Similarity	NPD6798	Discontinued
0.6627	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD447	Suspended
0.66	Remote Similarity	NPD2491	Approved
0.659	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4110	Phase 3
0.659	Remote Similarity	NPD7003	Approved
0.6588	Remote Similarity	NPD1510	Phase 2
0.6587	Remote Similarity	NPD6233	Phase 2
0.6587	Remote Similarity	NPD8032	Phase 2
0.6583	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6534	Approved
0.6582	Remote Similarity	NPD6535	Approved
0.6571	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3887	Approved
0.6552	Remote Similarity	NPD2354	Approved
0.6552	Remote Similarity	NPD2309	Approved
0.6543	Remote Similarity	NPD1608	Approved
0.6541	Remote Similarity	NPD5711	Approved
0.6541	Remote Similarity	NPD5710	Approved
0.654	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7028	Phase 2
0.653	Remote Similarity	NPD7048	Phase 3

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