NPASS Compound

Structure

NPC273668 OpenBabel07101719252D 41 45 0 0 1 0 0 0 0 0999 V2000 -1.6583 3.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1459 4.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7954 -0.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2741 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7954 -1.0857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2741 -1.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8292 -2.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8292 0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4875 4.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 -1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4875 -0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4875 -3.3511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 -2.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4875 -0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3167 0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6583 2.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3167 3.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 -0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6583 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4875 -1.4362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8292 -1.4362 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3167 -2.8723 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4875 1.4362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8292 1.4362 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3167 2.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3167 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3167 -1.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 -1.9149 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8292 -0.4787 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 -1.6583 0.9574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4875 3.3511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1459 -3.3511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8292 1.4362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 2.3936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1459 2.3936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4875 2.3936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 20 1 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 8 33 1 0 0 0 0 10 20 2 0 0 0 0 11 12 1 0 0 0 0 11 21 2 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 32 1 0 0 0 0 16 33 1 0 0 0 0 17 22 1 0 0 0 0 17 30 1 0 0 0 0 18 26 1 0 0 0 0 18 30 1 0 0 0 0 19 36 1 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 21 34 1 0 0 0 0 22 35 1 6 0 0 0 23 31 1 0 0 0 0 23 32 1 1 0 0 0 24 32 1 1 0 0 0 24 33 1 0 0 0 0 25 31 1 0 0 0 0 25 37 1 1 0 0 0 26 35 1 6 0 0 0 26 41 1 0 0 0 0 27 28 1 0 0 0 0 27 34 1 6 0 0 0 27 38 1 0 0 0 0 28 35 1 6 0 0 0 28 39 1 0 0 0 0 29 40 2 0 0 0 0 29 41 1 0 0 0 0 32 7 1 1 0 0 0 33 34 1 6 0 0 0 34 9 1 6 0 0 0 35 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.41
Volume:	615.966
LogP:	5.065
LogD:	4.5
LogS:	-4.416
# Rotatable Bonds:	4
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.2
Synthetic Accessibility Score:	5.352
Fsp3:	0.857
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:	-5.009
MDCK Permeability:	2.8468199161579832e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.384
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	91.34601593017578%
Volume Distribution (VD):	1.075
Pgp-substrate:	3.7457685470581055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.33
CYP2C9-substrate:	0.134
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.595
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	6.486
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.231
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.581
Carcinogencity:	0.094
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC273668

Natural Product ID:	NPC273668
*Common Name:**	JIXNEPDMGSNJOM-AUBQSUGRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JIXNEPDMGSNJOM-AUBQSUGRSA-N
Standard InCHI:	InChI=1S/C35H56O6/c1-10-20(2)29(40)41-26-18-30(3,4)17-22-21-11-12-24-32(7)15-14-25(37)31(5,6)23(32)13-16-33(24,8)34(21,9)27(38)28(39)35(22,26)19-36/h10-11,22-28,36-39H,12-19H2,1-9H3/b20-10-/t22-,23-,24+,25-,26-,27-,28+,32-,33+,34-,35+/m0/s1
SMILES:	C/C=C(C(=O)O[C@H]1CC(C)(C)C[C@@H]2[C@@]1(CO)[C@H](O)[C@H](O)[C@@]1(C2=CC[C@H]2[C@@]1(C)CC[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)O)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632935
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33464	cyrilla racemiflora	Species	Cyrillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26422131]
NPO40059	Camellia crapnelliana	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29064696]

☑ 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	2
Others	1

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	8700.0	nM	PMID[524130]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	2560.0	nM	PMID[524131]
NPT21742	CELL-LINE	L02	Homo sapiens	Activity	>	90.0	%	PMID[524131]

☑ 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 NPC273668 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	230
0.1-0.2	1435
0.2-0.3	4225
0.3-0.4	9112
0.4-0.5	13011
0.5-0.6	6634
0.6-0.7	5118
0.7-0.8	2619
0.8-0.85	255
0.85-0.9	46
0.9-0.95	2
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC283343
0.9789	High Similarity	NPC258547
0.9787	High Similarity	NPC474190
0.9691	High Similarity	NPC88349
0.9684	High Similarity	NPC473160
0.9495	High Similarity	NPC475263
0.9394	High Similarity	NPC473586
0.8788	High Similarity	NPC476195
0.8713	High Similarity	NPC476889
0.87	High Similarity	NPC235920
0.87	High Similarity	NPC96784
0.87	High Similarity	NPC476132
0.8692	High Similarity	NPC268954
0.8624	High Similarity	NPC470914
0.8614	High Similarity	NPC476890
0.8614	High Similarity	NPC40918
0.86	High Similarity	NPC473510
0.8598	High Similarity	NPC110861
0.8532	High Similarity	NPC470515
0.8519	High Similarity	NPC44170
0.8515	High Similarity	NPC54909
0.8515	High Similarity	NPC93744
0.8515	High Similarity	NPC476888
0.8515	High Similarity	NPC233012
0.8511	High Similarity	NPC84121
0.8511	High Similarity	NPC137306
0.85	High Similarity	NPC477876
0.85	High Similarity	NPC247233
0.85	High Similarity	NPC477875
0.8485	Intermediate Similarity	NPC173744
0.8485	Intermediate Similarity	NPC88009
0.8485	Intermediate Similarity	NPC230151
0.8485	Intermediate Similarity	NPC204961
0.8485	Intermediate Similarity	NPC73004
0.8469	Intermediate Similarity	NPC299996
0.8469	Intermediate Similarity	NPC231063
0.8469	Intermediate Similarity	NPC145667
0.8469	Intermediate Similarity	NPC88116
0.8469	Intermediate Similarity	NPC91010
0.8469	Intermediate Similarity	NPC282395
0.8469	Intermediate Similarity	NPC215700
0.8469	Intermediate Similarity	NPC32407
0.8469	Intermediate Similarity	NPC263548
0.8469	Intermediate Similarity	NPC20235
0.8462	Intermediate Similarity	NPC301666
0.8455	Intermediate Similarity	NPC470517
0.8455	Intermediate Similarity	NPC470911
0.8455	Intermediate Similarity	NPC470915
0.8416	Intermediate Similarity	NPC254567
0.8416	Intermediate Similarity	NPC230546
0.8416	Intermediate Similarity	NPC474571
0.8404	Intermediate Similarity	NPC191965
0.84	Intermediate Similarity	NPC247139
0.84	Intermediate Similarity	NPC210337
0.84	Intermediate Similarity	NPC255589
0.84	Intermediate Similarity	NPC51499
0.84	Intermediate Similarity	NPC9613
0.84	Intermediate Similarity	NPC259788
0.8384	Intermediate Similarity	NPC96916
0.8384	Intermediate Similarity	NPC32118
0.8367	Intermediate Similarity	NPC136313
0.8367	Intermediate Similarity	NPC53555
0.8367	Intermediate Similarity	NPC74855
0.8367	Intermediate Similarity	NPC86368
0.8367	Intermediate Similarity	NPC307335
0.8351	Intermediate Similarity	NPC78973
0.835	Intermediate Similarity	NPC474124
0.8333	Intermediate Similarity	NPC473159
0.8333	Intermediate Similarity	NPC475617
0.8317	Intermediate Similarity	NPC29765
0.8317	Intermediate Similarity	NPC275086
0.8317	Intermediate Similarity	NPC325229
0.8317	Intermediate Similarity	NPC111214
0.8317	Intermediate Similarity	NPC271614
0.83	Intermediate Similarity	NPC25848
0.83	Intermediate Similarity	NPC201657
0.83	Intermediate Similarity	NPC305464
0.83	Intermediate Similarity	NPC327179
0.83	Intermediate Similarity	NPC259733
0.83	Intermediate Similarity	NPC307282
0.83	Intermediate Similarity	NPC207922
0.83	Intermediate Similarity	NPC473153
0.83	Intermediate Similarity	NPC158371
0.83	Intermediate Similarity	NPC19376
0.8298	Intermediate Similarity	NPC238992
0.8288	Intermediate Similarity	NPC473839
0.8288	Intermediate Similarity	NPC77689
0.8288	Intermediate Similarity	NPC211093
0.8288	Intermediate Similarity	NPC473636
0.8283	Intermediate Similarity	NPC296164
0.8283	Intermediate Similarity	NPC74751
0.8283	Intermediate Similarity	NPC87095
0.8273	Intermediate Similarity	NPC475809
0.8273	Intermediate Similarity	NPC134430
0.8265	Intermediate Similarity	NPC72845
0.8265	Intermediate Similarity	NPC235884
0.8265	Intermediate Similarity	NPC470590
0.8265	Intermediate Similarity	NPC300351
0.8265	Intermediate Similarity	NPC77099
0.8265	Intermediate Similarity	NPC52021
0.8265	Intermediate Similarity	NPC306541
0.8265	Intermediate Similarity	NPC60755
0.8265	Intermediate Similarity	NPC71074
0.8265	Intermediate Similarity	NPC285184
0.8265	Intermediate Similarity	NPC25299
0.8265	Intermediate Similarity	NPC84319
0.8265	Intermediate Similarity	NPC472149
0.8252	Intermediate Similarity	NPC475344
0.8252	Intermediate Similarity	NPC472552
0.8252	Intermediate Similarity	NPC476471
0.8247	Intermediate Similarity	NPC82876
0.8235	Intermediate Similarity	NPC35239
0.8235	Intermediate Similarity	NPC38855
0.8218	Intermediate Similarity	NPC175351
0.8218	Intermediate Similarity	NPC26413
0.8218	Intermediate Similarity	NPC224356
0.8218	Intermediate Similarity	NPC132753
0.8218	Intermediate Similarity	NPC73911
0.8218	Intermediate Similarity	NPC121402
0.8218	Intermediate Similarity	NPC43686
0.8218	Intermediate Similarity	NPC106112
0.8218	Intermediate Similarity	NPC261935
0.8218	Intermediate Similarity	NPC151681
0.8208	Intermediate Similarity	NPC88701
0.8208	Intermediate Similarity	NPC473483
0.8208	Intermediate Similarity	NPC189075
0.8208	Intermediate Similarity	NPC275539
0.82	Intermediate Similarity	NPC195715
0.82	Intermediate Similarity	NPC276110
0.8191	Intermediate Similarity	NPC132386
0.8191	Intermediate Similarity	NPC253402
0.8191	Intermediate Similarity	NPC159168
0.819	Intermediate Similarity	NPC477877
0.8182	Intermediate Similarity	NPC214756
0.8182	Intermediate Similarity	NPC133579
0.8182	Intermediate Similarity	NPC169343
0.8182	Intermediate Similarity	NPC272075
0.8182	Intermediate Similarity	NPC474806
0.8182	Intermediate Similarity	NPC295643
0.8182	Intermediate Similarity	NPC162615
0.8182	Intermediate Similarity	NPC275809
0.8182	Intermediate Similarity	NPC38232
0.8182	Intermediate Similarity	NPC229281
0.8182	Intermediate Similarity	NPC205034
0.8182	Intermediate Similarity	NPC152778
0.8173	Intermediate Similarity	NPC281378
0.8163	Intermediate Similarity	NPC111110
0.8163	Intermediate Similarity	NPC130278
0.8163	Intermediate Similarity	NPC474728
0.8163	Intermediate Similarity	NPC120840
0.8163	Intermediate Similarity	NPC126369
0.8163	Intermediate Similarity	NPC221111
0.8163	Intermediate Similarity	NPC280149
0.8163	Intermediate Similarity	NPC49320
0.8163	Intermediate Similarity	NPC113989
0.8163	Intermediate Similarity	NPC470589
0.8155	Intermediate Similarity	NPC11974
0.8155	Intermediate Similarity	NPC235142
0.8155	Intermediate Similarity	NPC472554
0.8155	Intermediate Similarity	NPC256247
0.8137	Intermediate Similarity	NPC478056
0.8137	Intermediate Similarity	NPC218107
0.8137	Intermediate Similarity	NPC471966
0.8137	Intermediate Similarity	NPC159763
0.8137	Intermediate Similarity	NPC92275
0.8137	Intermediate Similarity	NPC260149
0.8137	Intermediate Similarity	NPC124512
0.8137	Intermediate Similarity	NPC58942
0.8137	Intermediate Similarity	NPC278386
0.8131	Intermediate Similarity	NPC475586
0.8131	Intermediate Similarity	NPC310546
0.8125	Intermediate Similarity	NPC131813
0.8125	Intermediate Similarity	NPC475069
0.8125	Intermediate Similarity	NPC237344
0.8125	Intermediate Similarity	NPC175145
0.8119	Intermediate Similarity	NPC88847
0.8119	Intermediate Similarity	NPC116457
0.8119	Intermediate Similarity	NPC473158
0.8119	Intermediate Similarity	NPC16967
0.8119	Intermediate Similarity	NPC472362
0.8119	Intermediate Similarity	NPC98874
0.8119	Intermediate Similarity	NPC472363
0.8119	Intermediate Similarity	NPC154526
0.8113	Intermediate Similarity	NPC475570
0.8113	Intermediate Similarity	NPC110496
0.8108	Intermediate Similarity	NPC473968
0.8108	Intermediate Similarity	NPC473405
0.81	Intermediate Similarity	NPC191412
0.81	Intermediate Similarity	NPC184006
0.81	Intermediate Similarity	NPC6818
0.81	Intermediate Similarity	NPC78580
0.81	Intermediate Similarity	NPC114159
0.81	Intermediate Similarity	NPC23621
0.8095	Intermediate Similarity	NPC473543
0.8091	Intermediate Similarity	NPC147912
0.8091	Intermediate Similarity	NPC67259
0.8085	Intermediate Similarity	NPC304285
0.8085	Intermediate Similarity	NPC286786
0.8085	Intermediate Similarity	NPC47763
0.8081	Intermediate Similarity	NPC65120

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 NPC273668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1618
0.2-0.3	3703
0.3-0.4	2386
0.4-0.5	803
0.5-0.6	259
0.6-0.7	149
0.7-0.8	28
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
0.8283	Intermediate Similarity	NPD7748	Approved
0.8218	Intermediate Similarity	NPD7902	Approved
0.8137	Intermediate Similarity	NPD4225	Approved
0.8081	Intermediate Similarity	NPD7515	Phase 2
0.7961	Intermediate Similarity	NPD7638	Approved
0.7921	Intermediate Similarity	NPD7900	Approved
0.7921	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7640	Approved
0.7885	Intermediate Similarity	NPD7639	Approved
0.7788	Intermediate Similarity	NPD7115	Discovery
0.7766	Intermediate Similarity	NPD7645	Phase 2
0.7672	Intermediate Similarity	NPD8033	Approved
0.7586	Intermediate Similarity	NPD8377	Approved
0.7586	Intermediate Similarity	NPD8294	Approved
0.7521	Intermediate Similarity	NPD8378	Approved
0.7521	Intermediate Similarity	NPD8379	Approved
0.7521	Intermediate Similarity	NPD8296	Approved
0.7521	Intermediate Similarity	NPD8380	Approved
0.7521	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.7477	Intermediate Similarity	NPD5344	Discontinued
0.7477	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7328	Approved
0.7414	Intermediate Similarity	NPD7327	Approved
0.7387	Intermediate Similarity	NPD6686	Approved
0.7373	Intermediate Similarity	NPD7503	Approved
0.7281	Intermediate Similarity	NPD8297	Approved
0.725	Intermediate Similarity	NPD8328	Phase 3
0.7248	Intermediate Similarity	NPD7632	Discontinued
0.7232	Intermediate Similarity	NPD6881	Approved
0.7232	Intermediate Similarity	NPD6899	Approved
0.7212	Intermediate Similarity	NPD8035	Phase 2
0.7212	Intermediate Similarity	NPD8034	Phase 2
0.7207	Intermediate Similarity	NPD7128	Approved
0.7207	Intermediate Similarity	NPD5739	Approved
0.7207	Intermediate Similarity	NPD6675	Approved
0.7207	Intermediate Similarity	NPD6402	Approved
0.7193	Intermediate Similarity	NPD8130	Phase 1
0.7168	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD5697	Approved
0.7131	Intermediate Similarity	NPD7507	Approved
0.7115	Intermediate Similarity	NPD7838	Discovery
0.7105	Intermediate Similarity	NPD6883	Approved
0.7105	Intermediate Similarity	NPD7290	Approved
0.7105	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7102	Approved
0.708	Intermediate Similarity	NPD7320	Approved
0.7064	Intermediate Similarity	NPD6648	Approved
0.7043	Intermediate Similarity	NPD6869	Approved
0.7043	Intermediate Similarity	NPD6650	Approved
0.7043	Intermediate Similarity	NPD6847	Approved
0.7043	Intermediate Similarity	NPD6649	Approved
0.7043	Intermediate Similarity	NPD6617	Approved
0.7034	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6012	Approved
0.7018	Intermediate Similarity	NPD6373	Approved
0.7018	Intermediate Similarity	NPD6372	Approved
0.7018	Intermediate Similarity	NPD6013	Approved
0.7018	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5701	Approved
0.6983	Remote Similarity	NPD6882	Approved
0.697	Remote Similarity	NPD7525	Registered
0.6961	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7319	Approved
0.693	Remote Similarity	NPD6011	Approved
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8133	Approved
0.6893	Remote Similarity	NPD3618	Phase 1
0.6887	Remote Similarity	NPD6079	Approved
0.6881	Remote Similarity	NPD6083	Phase 2
0.6881	Remote Similarity	NPD6084	Phase 2
0.6863	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6051	Approved
0.6857	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5328	Approved
0.6842	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6412	Phase 2
0.6827	Remote Similarity	NPD3573	Approved
0.6796	Remote Similarity	NPD1694	Approved
0.6792	Remote Similarity	NPD6698	Approved
0.6792	Remote Similarity	NPD46	Approved
0.6786	Remote Similarity	NPD5211	Phase 2
0.6783	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4632	Approved
0.6757	Remote Similarity	NPD5286	Approved
0.6757	Remote Similarity	NPD4696	Approved
0.6757	Remote Similarity	NPD5285	Approved
0.6752	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7736	Approved
0.6731	Remote Similarity	NPD6409	Approved
0.6731	Remote Similarity	NPD5330	Approved
0.6731	Remote Similarity	NPD7521	Approved
0.6731	Remote Similarity	NPD6684	Approved
0.6731	Remote Similarity	NPD7334	Approved
0.6731	Remote Similarity	NPD7146	Approved
0.6729	Remote Similarity	NPD6411	Approved
0.6727	Remote Similarity	NPD4755	Approved
0.6721	Remote Similarity	NPD6319	Approved
0.6699	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6637	Remote Similarity	NPD4633	Approved
0.6637	Remote Similarity	NPD5225	Approved
0.6637	Remote Similarity	NPD5224	Approved
0.6637	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD5222	Approved
0.6636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7339	Approved
0.6633	Remote Similarity	NPD6942	Approved
0.6607	Remote Similarity	NPD4700	Approved
0.6604	Remote Similarity	NPD6672	Approved
0.6604	Remote Similarity	NPD6903	Approved
0.6604	Remote Similarity	NPD5737	Approved
0.6579	Remote Similarity	NPD5174	Approved
0.6579	Remote Similarity	NPD5175	Approved
0.6577	Remote Similarity	NPD5173	Approved
0.6574	Remote Similarity	NPD7637	Suspended
0.6566	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6335	Approved
0.6555	Remote Similarity	NPD6053	Discontinued
0.6549	Remote Similarity	NPD5223	Approved
0.6549	Remote Similarity	NPD4159	Approved
0.6545	Remote Similarity	NPD5695	Phase 3
0.6542	Remote Similarity	NPD6101	Approved
0.6542	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3666	Approved
0.6538	Remote Similarity	NPD3133	Approved
0.6538	Remote Similarity	NPD3665	Phase 1
0.6532	Remote Similarity	NPD8516	Approved
0.6532	Remote Similarity	NPD8513	Phase 3
0.6532	Remote Similarity	NPD8517	Approved
0.6532	Remote Similarity	NPD8515	Approved
0.6529	Remote Similarity	NPD6868	Approved
0.6525	Remote Similarity	NPD4634	Approved
0.6518	Remote Similarity	NPD5696	Approved
0.6518	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5778	Approved
0.6514	Remote Similarity	NPD5779	Approved
0.6509	Remote Similarity	NPD7524	Approved
0.6508	Remote Similarity	NPD7492	Approved
0.6486	Remote Similarity	NPD7732	Phase 3
0.6486	Remote Similarity	NPD4697	Phase 3
0.6486	Remote Similarity	NPD7614	Phase 1
0.6475	Remote Similarity	NPD6009	Approved
0.6475	Remote Similarity	NPD6317	Approved
0.6471	Remote Similarity	NPD4695	Discontinued
0.6466	Remote Similarity	NPD6008	Approved
0.6465	Remote Similarity	NPD8264	Approved
0.6457	Remote Similarity	NPD6616	Approved
0.6452	Remote Similarity	NPD6054	Approved
0.6429	Remote Similarity	NPD7604	Phase 2
0.6423	Remote Similarity	NPD6313	Approved
0.6423	Remote Similarity	NPD6314	Approved
0.6422	Remote Similarity	NPD5693	Phase 1
0.6406	Remote Similarity	NPD8293	Discontinued
0.6406	Remote Similarity	NPD7078	Approved
0.6403	Remote Similarity	NPD8166	Discontinued
0.64	Remote Similarity	NPD6908	Approved
0.64	Remote Similarity	NPD6909	Approved
0.64	Remote Similarity	NPD5983	Phase 2
0.6396	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4753	Phase 2
0.6387	Remote Similarity	NPD6371	Approved
0.6381	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4730	Approved
0.6356	Remote Similarity	NPD5128	Approved
0.6356	Remote Similarity	NPD4729	Approved
0.6349	Remote Similarity	NPD6370	Approved
0.6333	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5785	Approved
0.6328	Remote Similarity	NPD6336	Discontinued
0.6325	Remote Similarity	NPD4767	Approved
0.6325	Remote Similarity	NPD4768	Approved
0.632	Remote Similarity	NPD6059	Approved
0.6293	Remote Similarity	NPD4754	Approved
0.6286	Remote Similarity	NPD6695	Phase 3
0.6271	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6016	Approved
0.627	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6015	Approved
0.6262	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD4629	Approved
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.6239	Remote Similarity	NPD6673	Approved
0.6239	Remote Similarity	NPD6904	Approved
0.6239	Remote Similarity	NPD6080	Approved
0.6238	Remote Similarity	NPD6933	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