NPASS Compound

Structure

NPC82851 OpenBabel07101718182D 43 47 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 2.9263 -1.1266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7702 1.2022 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 -1.6026 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 2.0253 -1.5605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6955 0.2050 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 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 1.2738 0.0000 0.0000 C 0 0 1 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 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 2.0259 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 1.9506 -2.5577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5217 -0.3583 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 1.1991 -0.9972 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 17 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 8 38 1 0 0 0 0 9 10 2 0 0 0 0 9 18 1 0 0 0 0 10 39 1 0 0 0 0 11 19 1 0 0 0 0 11 21 1 0 0 0 0 12 20 1 0 0 0 0 12 28 1 0 0 0 0 13 22 1 0 0 0 0 14 18 2 0 0 0 0 14 39 1 0 0 0 0 15 30 1 0 0 0 0 15 31 1 0 0 0 0 16 32 2 0 0 0 0 16 40 1 0 0 0 0 17 33 2 0 0 0 0 17 41 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 0 0 0 0 19 29 1 1 0 0 0 20 31 1 0 0 0 0 20 34 2 0 0 0 0 21 35 2 0 0 0 0 21 38 1 0 0 0 0 22 36 2 0 0 0 0 22 42 1 0 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 23 40 1 6 0 0 0 24 28 1 1 0 0 0 24 42 1 0 0 0 0 25 27 1 0 0 0 0 25 41 1 6 0 0 0 26 29 1 6 0 0 0 26 43 1 0 0 0 0 28 30 1 1 0 0 0 29 31 1 6 0 0 0 30 13 1 1 0 0 0 30 43 1 0 0 0 0 31 37 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.24
Volume:	586.341
LogP:	2.967
LogD:	1.897
LogS:	-4.665
# Rotatable Bonds:	8
TPSA:	164.87
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	6.591
Fsp3:	0.645
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:	-5.373
MDCK Permeability:	6.735377974109724e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.365
Human Intestinal Absorption (HIA):	0.961
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.701
Plasma Protein Binding (PPB):	64.191162109375%
Volume Distribution (VD):	0.888
Pgp-substrate:	37.84151077270508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.069
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.727
CYP3A4-substrate:	0.709

ADMET: Excretion

Clearance (CL):	5.101
Half-life (T1/2):	0.602

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.865
Drug-inuced Liver Injury (DILI):	0.888
AMES Toxicity:	0.149
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.153
Carcinogencity:	0.654
Eye Corrosion:	0.019
Eye Irritation:	0.033
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC82851

Natural Product ID:	NPC82851
*Common Name:**	Cipadesin P
IUPAC Name:	n.a.
Synonyms:	Cipadesin P
Standard InCHIKey:	QVQCIENRINYMCG-BKPMUCPTSA-N
Standard InCHI:	InChI=1S/C31H38O12/c1-15-30-13-22(36)42-24(18-9-10-39-14-18)28(30,6)12-20(34)31(15,37)29(7)19(11-21(35)38-8)27(4,5)25(41-17(3)33)23(26(29)43-30)40-16(2)32/h9-10,14,19,23-26,37H,1,11-13H2,2-8H3/t19-,23-,24-,25+,26-,28-,29+,30-,31-/m0/s1
SMILES:	COC(=O)C[C@H]1C(C)(C)[C@H](OC(=O)C)[C@@H]([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)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215113
PubChem CID:	46918647
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
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[525694]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[525694]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[525694]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[525694]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[525694]

☑ 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 NPC82851 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	358
0.1-0.2	1428
0.2-0.3	3187
0.3-0.4	5345
0.4-0.5	9804
0.5-0.6	9772
0.6-0.7	8225
0.7-0.8	4059
0.8-0.85	317
0.85-0.9	127
0.9-0.95	69
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9801	High Similarity	NPC249021
0.9613	High Similarity	NPC470940
0.961	High Similarity	NPC200782
0.9603	High Similarity	NPC282445
0.9548	High Similarity	NPC292389
0.9548	High Similarity	NPC477405
0.9548	High Similarity	NPC469338
0.9536	High Similarity	NPC476201
0.949	High Similarity	NPC173516
0.9487	High Similarity	NPC469849
0.9487	High Similarity	NPC276551
0.9487	High Similarity	NPC470182
0.943	High Similarity	NPC160651
0.943	High Similarity	NPC471397
0.9427	High Similarity	NPC470875
0.9423	High Similarity	NPC39986
0.9423	High Similarity	NPC302369
0.9423	High Similarity	NPC134254
0.9419	High Similarity	NPC472653
0.9412	High Similarity	NPC476262
0.9367	High Similarity	NPC472775
0.9367	High Similarity	NPC472774
0.9363	High Similarity	NPC271657
0.9359	High Similarity	NPC18347
0.9359	High Similarity	NPC149896
0.9359	High Similarity	NPC193798
0.9359	High Similarity	NPC472771
0.9359	High Similarity	NPC5079
0.9359	High Similarity	NPC69028
0.9359	High Similarity	NPC329938
0.9355	High Similarity	NPC477403
0.9355	High Similarity	NPC475967
0.9308	High Similarity	NPC271235
0.9299	High Similarity	NPC234660
0.9299	High Similarity	NPC472773
0.9299	High Similarity	NPC51568
0.9295	High Similarity	NPC335761
0.9295	High Similarity	NPC25255
0.9295	High Similarity	NPC477402
0.929	High Similarity	NPC261597
0.929	High Similarity	NPC286722
0.929	High Similarity	NPC36655
0.929	High Similarity	NPC45101
0.9281	High Similarity	NPC469503
0.9276	High Similarity	NPC476122
0.925	High Similarity	NPC82602
0.9245	High Similarity	NPC472282
0.9241	High Similarity	NPC476856
0.9241	High Similarity	NPC476858
0.9241	High Similarity	NPC476857
0.9236	High Similarity	NPC117986
0.9236	High Similarity	NPC263432
0.9236	High Similarity	NPC470939
0.9231	High Similarity	NPC473473
0.9231	High Similarity	NPC475295
0.9226	High Similarity	NPC209364
0.9226	High Similarity	NPC107646
0.9182	High Similarity	NPC97574
0.9182	High Similarity	NPC93172
0.9177	High Similarity	NPC88841
0.9177	High Similarity	NPC288602
0.9177	High Similarity	NPC469846
0.9172	High Similarity	NPC475381
0.9167	High Similarity	NPC299038
0.9167	High Similarity	NPC167142
0.9167	High Similarity	NPC472283
0.9167	High Similarity	NPC472772
0.9161	High Similarity	NPC469336
0.9161	High Similarity	NPC264943
0.9161	High Similarity	NPC44675
0.9161	High Similarity	NPC214541
0.9156	High Similarity	NPC44577
0.915	High Similarity	NPC196864
0.915	High Similarity	NPC477404
0.9125	High Similarity	NPC476861
0.9125	High Similarity	NPC476853
0.9125	High Similarity	NPC472651
0.9125	High Similarity	NPC476850
0.9119	High Similarity	NPC123088
0.9119	High Similarity	NPC476860
0.9114	High Similarity	NPC207978
0.9114	High Similarity	NPC290400
0.9114	High Similarity	NPC188649
0.9114	High Similarity	NPC96443
0.9103	High Similarity	NPC126723
0.9103	High Similarity	NPC469485
0.9097	High Similarity	NPC178932
0.9097	High Similarity	NPC30222
0.9079	High Similarity	NPC255414
0.9074	High Similarity	NPC160818
0.9074	High Similarity	NPC169299
0.9068	High Similarity	NPC472652
0.9068	High Similarity	NPC296558
0.9062	High Similarity	NPC23387
0.9057	High Similarity	NPC198047
0.9057	High Similarity	NPC476197
0.9051	High Similarity	NPC305016
0.9045	High Similarity	NPC187149
0.9045	High Similarity	NPC173544
0.9038	High Similarity	NPC35000
0.9026	High Similarity	NPC159927
0.9026	High Similarity	NPC469335
0.8994	High Similarity	NPC211777
0.8987	High Similarity	NPC237155
0.8987	High Similarity	NPC307383
0.8981	High Similarity	NPC60973
0.897	High Similarity	NPC478177
0.8968	High Similarity	NPC18135
0.8963	High Similarity	NPC236004
0.8963	High Similarity	NPC94763
0.8961	High Similarity	NPC69647
0.8961	High Similarity	NPC125182
0.8954	High Similarity	NPC470941
0.8944	High Similarity	NPC472141
0.8938	High Similarity	NPC663
0.8938	High Similarity	NPC472139
0.8938	High Similarity	NPC419
0.8938	High Similarity	NPC224394
0.8924	High Similarity	NPC472776
0.8924	High Similarity	NPC472777
0.8924	High Similarity	NPC472778
0.8924	High Similarity	NPC88007
0.8924	High Similarity	NPC195954
0.8917	High Similarity	NPC281258
0.8917	High Similarity	NPC469850
0.8909	High Similarity	NPC262386
0.8896	High Similarity	NPC470995
0.8889	High Similarity	NPC473766
0.8889	High Similarity	NPC473753
0.8882	High Similarity	NPC476944
0.8875	High Similarity	NPC68848
0.8868	High Similarity	NPC262872
0.8868	High Similarity	NPC474611
0.8868	High Similarity	NPC475226
0.8861	High Similarity	NPC263265
0.8855	High Similarity	NPC472665
0.8848	High Similarity	NPC471437
0.8827	High Similarity	NPC149945
0.8827	High Similarity	NPC475779
0.8827	High Similarity	NPC121995
0.8827	High Similarity	NPC478178
0.882	High Similarity	NPC165218
0.8816	High Similarity	NPC243577
0.8812	High Similarity	NPC470789
0.8812	High Similarity	NPC191828
0.8805	High Similarity	NPC194499
0.8805	High Similarity	NPC470118
0.879	High Similarity	NPC268905
0.8782	High Similarity	NPC46551
0.8773	High Similarity	NPC270312
0.8773	High Similarity	NPC472764
0.8773	High Similarity	NPC100333
0.8766	High Similarity	NPC262198
0.8766	High Similarity	NPC346
0.8758	High Similarity	NPC470792
0.8758	High Similarity	NPC18986
0.875	High Similarity	NPC470938
0.875	High Similarity	NPC121158
0.8742	High Similarity	NPC41880
0.8735	High Similarity	NPC469576
0.8734	High Similarity	NPC57998
0.8727	High Similarity	NPC285227
0.872	High Similarity	NPC327922
0.872	High Similarity	NPC472765
0.872	High Similarity	NPC472766
0.8718	High Similarity	NPC472654
0.8718	High Similarity	NPC211625
0.8718	High Similarity	NPC195325
0.871	High Similarity	NPC250228
0.871	High Similarity	NPC221809
0.8704	High Similarity	NPC285567
0.8701	High Similarity	NPC5676
0.8701	High Similarity	NPC41182
0.8696	High Similarity	NPC287559
0.8696	High Similarity	NPC8389
0.8693	High Similarity	NPC476946
0.8683	High Similarity	NPC469633
0.8671	High Similarity	NPC33938
0.8671	High Similarity	NPC75906
0.8671	High Similarity	NPC472672
0.8667	High Similarity	NPC302392
0.8662	High Similarity	NPC212257
0.8662	High Similarity	NPC156189
0.8659	High Similarity	NPC478179
0.8659	High Similarity	NPC476224
0.865	High Similarity	NPC56358
0.865	High Similarity	NPC146991
0.8642	High Similarity	NPC79571
0.8642	High Similarity	NPC472668
0.8642	High Similarity	NPC472767
0.8636	High Similarity	NPC137295
0.8636	High Similarity	NPC251865
0.8623	High Similarity	NPC471632
0.8616	High Similarity	NPC302054
0.8616	High Similarity	NPC114880
0.8616	High Similarity	NPC253201
0.8614	High Similarity	NPC159232
0.8609	High Similarity	NPC476943
0.8598	High Similarity	NPC214600
0.8589	High Similarity	NPC283209

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 NPC82851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	1022
0.2-0.3	2132
0.3-0.4	2600
0.4-0.5	1872
0.5-0.6	887
0.6-0.7	269
0.7-0.8	58
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8647	High Similarity	NPD8434	Phase 2
0.8562	High Similarity	NPD5760	Phase 2
0.8562	High Similarity	NPD5761	Phase 2
0.8024	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7075	Discontinued
0.7784	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6764	Approved
0.7727	Intermediate Similarity	NPD6765	Approved
0.7679	Intermediate Similarity	NPD7819	Suspended
0.7661	Intermediate Similarity	NPD5494	Approved
0.7654	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6559	Discontinued
0.7605	Intermediate Similarity	NPD6599	Discontinued
0.7556	Intermediate Similarity	NPD6784	Approved
0.7556	Intermediate Similarity	NPD6785	Approved
0.7544	Intermediate Similarity	NPD3749	Approved
0.7541	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD8404	Phase 2
0.7486	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5844	Phase 1
0.7456	Intermediate Similarity	NPD7411	Suspended
0.7443	Intermediate Similarity	NPD7473	Discontinued
0.7427	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5402	Approved
0.7427	Intermediate Similarity	NPD3817	Phase 2
0.7399	Intermediate Similarity	NPD919	Approved
0.7396	Intermediate Similarity	NPD4380	Phase 2
0.7384	Intermediate Similarity	NPD3882	Suspended
0.7374	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6799	Approved
0.7348	Intermediate Similarity	NPD8313	Approved
0.7348	Intermediate Similarity	NPD8312	Approved
0.7341	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7251	Discontinued
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.7321	Intermediate Similarity	NPD920	Approved
0.7321	Intermediate Similarity	NPD5403	Approved
0.7318	Intermediate Similarity	NPD7074	Phase 3
0.7314	Intermediate Similarity	NPD6959	Discontinued
0.731	Intermediate Similarity	NPD1934	Approved
0.7305	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3818	Discontinued
0.7293	Intermediate Similarity	NPD7808	Phase 3
0.7293	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6797	Phase 2
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6232	Discontinued
0.7263	Intermediate Similarity	NPD7054	Approved
0.7235	Intermediate Similarity	NPD3226	Approved
0.7222	Intermediate Similarity	NPD7472	Approved
0.7216	Intermediate Similarity	NPD8127	Discontinued
0.7216	Intermediate Similarity	NPD1247	Approved
0.7207	Intermediate Similarity	NPD3751	Discontinued
0.7202	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5401	Approved
0.7202	Intermediate Similarity	NPD2532	Approved
0.7202	Intermediate Similarity	NPD2533	Approved
0.7202	Intermediate Similarity	NPD2534	Approved
0.7195	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1465	Phase 2
0.7152	Intermediate Similarity	NPD1549	Phase 2
0.715	Intermediate Similarity	NPD7435	Discontinued
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD3926	Phase 2
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7111	Intermediate Similarity	NPD7228	Approved
0.7111	Intermediate Similarity	NPD7799	Discontinued
0.711	Intermediate Similarity	NPD37	Approved
0.7108	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2346	Discontinued
0.7091	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1471	Phase 3
0.7086	Intermediate Similarity	NPD4967	Phase 2
0.7086	Intermediate Similarity	NPD4965	Approved
0.7086	Intermediate Similarity	NPD4966	Approved
0.7086	Intermediate Similarity	NPD7768	Phase 2
0.7083	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7236	Approved
0.7079	Intermediate Similarity	NPD3787	Discontinued
0.7069	Intermediate Similarity	NPD2801	Approved
0.7066	Intermediate Similarity	NPD3750	Approved
0.7062	Intermediate Similarity	NPD7697	Approved
0.7062	Intermediate Similarity	NPD7696	Phase 3
0.7062	Intermediate Similarity	NPD7698	Approved
0.7059	Intermediate Similarity	NPD6273	Approved
0.7035	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1551	Phase 2
0.703	Intermediate Similarity	NPD2796	Approved
0.7027	Intermediate Similarity	NPD8407	Phase 2
0.701	Intermediate Similarity	NPD7907	Approved
0.7006	Intermediate Similarity	NPD2800	Approved
0.7006	Intermediate Similarity	NPD6234	Discontinued
0.6995	Remote Similarity	NPD6780	Approved
0.6995	Remote Similarity	NPD6777	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD6782	Approved
0.6995	Remote Similarity	NPD6781	Approved
0.6995	Remote Similarity	NPD6776	Approved
0.6977	Remote Similarity	NPD7239	Suspended
0.697	Remote Similarity	NPD2799	Discontinued
0.6968	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1512	Approved
0.6957	Remote Similarity	NPD8368	Discontinued
0.6957	Remote Similarity	NPD7685	Pre-registration
0.6946	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7871	Phase 2
0.6939	Remote Similarity	NPD8320	Phase 1
0.6939	Remote Similarity	NPD8319	Approved
0.6939	Remote Similarity	NPD7870	Phase 2
0.6935	Remote Similarity	NPD7874	Approved
0.6935	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7701	Phase 2
0.6912	Remote Similarity	NPD4111	Phase 1
0.6912	Remote Similarity	NPD4665	Approved
0.6905	Remote Similarity	NPD1243	Approved
0.689	Remote Similarity	NPD6355	Discontinued
0.6886	Remote Similarity	NPD2344	Approved
0.6878	Remote Similarity	NPD8361	Approved
0.6878	Remote Similarity	NPD8360	Approved
0.6867	Remote Similarity	NPD1510	Phase 2
0.6867	Remote Similarity	NPD7033	Discontinued
0.6867	Remote Similarity	NPD3748	Approved
0.6865	Remote Similarity	NPD7240	Approved
0.6842	Remote Similarity	NPD1511	Approved
0.6833	Remote Similarity	NPD7199	Phase 2
0.6831	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2935	Discontinued
0.6824	Remote Similarity	NPD6190	Approved
0.6821	Remote Similarity	NPD4107	Approved
0.6816	Remote Similarity	NPD7801	Approved
0.681	Remote Similarity	NPD2313	Discontinued
0.681	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7097	Phase 1
0.6804	Remote Similarity	NPD7699	Phase 2
0.6804	Remote Similarity	NPD7700	Phase 2
0.6802	Remote Similarity	NPD7497	Discontinued
0.68	Remote Similarity	NPD8151	Discontinued
0.6796	Remote Similarity	NPD5710	Approved
0.6796	Remote Similarity	NPD5711	Approved
0.6796	Remote Similarity	NPD7229	Phase 3
0.679	Remote Similarity	NPD6832	Phase 2
0.6789	Remote Similarity	NPD8435	Approved
0.6788	Remote Similarity	NPD447	Suspended
0.678	Remote Similarity	NPD8455	Phase 2
0.6765	Remote Similarity	NPD7003	Approved
0.6753	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD3057	Approved
0.6747	Remote Similarity	NPD1607	Approved
0.6744	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6535	Approved
0.6736	Remote Similarity	NPD6534	Approved
0.6733	Remote Similarity	NPD7783	Phase 2
0.6733	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1240	Approved
0.6725	Remote Similarity	NPD2309	Approved
0.672	Remote Similarity	NPD5953	Discontinued
0.6707	Remote Similarity	NPD3268	Approved
0.6707	Remote Similarity	NPD3764	Approved
0.6703	Remote Similarity	NPD7286	Phase 2
0.6703	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4287	Approved
0.6701	Remote Similarity	NPD4482	Phase 3
0.6686	Remote Similarity	NPD5763	Approved
0.6686	Remote Similarity	NPD5762	Approved
0.6684	Remote Similarity	NPD8285	Discontinued
0.6667	Remote Similarity	NPD3533	Approved
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD2975	Approved
0.6667	Remote Similarity	NPD8485	Approved
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2973	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD2974	Approved
0.6667	Remote Similarity	NPD2972	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4580	Approved
0.6647	Remote Similarity	NPD6651	Approved
0.6646	Remote Similarity	NPD7095	Approved
0.663	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2403	Approved
0.6628	Remote Similarity	NPD3887	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