NPASS Compound

Structure

NPC473160 OpenBabel07101719132D 44 48 0 0 1 0 0 0 0 0999 V2000 4.9883 -2.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1569 -5.2800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9883 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1828 -3.7114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1428 -3.7114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8455 2.7514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8055 2.7514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9883 -3.8400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1569 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3255 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -2.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3255 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1569 -4.3200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1569 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -1.4400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4942 1.4400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6628 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1569 1.4400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6628 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4942 -2.4000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4942 -1.4400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3255 -3.8400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -2.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3255 1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.4800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8314 0.4800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6628 -0.9600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3255 0.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1569 -2.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9883 1.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 0.4800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 -4.3200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3255 -0.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3255 -2.8800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 33 1 0 0 0 0 9 35 1 0 0 0 0 11 21 2 0 0 0 0 12 13 1 0 0 0 0 12 23 2 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 34 1 0 0 0 0 17 35 1 0 0 0 0 18 24 1 0 0 0 0 18 32 1 0 0 0 0 19 28 1 0 0 0 0 19 36 1 0 0 0 0 20 38 1 0 0 0 0 21 31 1 0 0 0 0 22 39 2 0 0 0 0 22 43 1 0 0 0 0 23 24 1 0 0 0 0 23 36 1 0 0 0 0 24 37 1 1 0 0 0 25 33 1 0 0 0 0 25 34 1 6 0 0 0 26 34 1 6 0 0 0 26 35 1 0 0 0 0 27 33 1 0 0 0 0 27 40 1 6 0 0 0 28 37 1 1 0 0 0 28 41 1 0 0 0 0 29 30 1 0 0 0 0 29 32 1 0 0 0 0 29 44 1 6 0 0 0 30 37 1 1 0 0 0 30 43 1 0 0 0 0 31 42 2 0 0 0 0 31 44 1 0 0 0 0 34 8 1 6 0 0 0 35 36 1 1 0 0 0 36 10 1 1 0 0 0 37 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.42
Volume:	656.711
LogP:	5.088
LogD:	4.369
LogS:	-4.778
# Rotatable Bonds:	6
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	5.334
Fsp3:	0.838
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:	-5.167
MDCK Permeability:	4.3601419747574255e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.173
30% Bioavailability (F30%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219
Plasma Protein Binding (PPB):	88.64327239990234%
Volume Distribution (VD):	1.25
Pgp-substrate:	6.239764213562012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.408
CYP2C9-substrate:	0.112
CYP2D6-inhibitor:	0.238
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.736
CYP3A4-substrate:	0.468

ADMET: Excretion

Clearance (CL):	4.245
Half-life (T1/2):	0.396

ADMET: Toxicity

hERG Blockers:	0.583
Human Hepatotoxicity (H-HT):	0.509
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.402
Carcinogencity:	0.022
Eye Corrosion:	0.006
Eye Irritation:	0.04
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC473160

Natural Product ID:	NPC473160
*Common Name:**	QDFQOBGBAIDDCY-UEGUDRSVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QDFQOBGBAIDDCY-UEGUDRSVSA-N
Standard InCHI:	InChI=1S/C37H58O7/c1-11-21(2)31(42)44-29-30(43-22(3)39)37(20-38)24(18-32(29,4)5)23-12-13-26-34(8)16-15-27(40)33(6,7)25(34)14-17-35(26,9)36(23,10)19-28(37)41/h11-12,24-30,38,40-41H,13-20H2,1-10H3/b21-11-/t24-,25-,26+,27-,28+,29-,30-,34-,35+,36+,37-/m0/s1
SMILES:	C/C=C(C(=O)O[C@H]1[C@H](OC(=O)C)[C@]2(CO)[C@H](O)C[C@@]3(C(=CC[C@H]4[C@@]3(C)CC[C@@H]3[C@]4(C)CC[C@@H](C3(C)C)O)[C@@H]2CC1(C)C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632934
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]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	7800.0	nM	PMID[513060]

☑ 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 NPC473160 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	226
0.1-0.2	1446
0.2-0.3	4381
0.3-0.4	9619
0.4-0.5	12641
0.5-0.6	6365
0.6-0.7	5140
0.7-0.8	2557
0.8-0.85	274
0.85-0.9	37
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC258547
0.9894	High Similarity	NPC283343
0.9684	High Similarity	NPC273668
0.9588	High Similarity	NPC88349
0.9474	High Similarity	NPC474190
0.9394	High Similarity	NPC475263
0.9293	High Similarity	NPC473586
0.88	High Similarity	NPC476889
0.8788	High Similarity	NPC235920
0.8788	High Similarity	NPC96784
0.8774	High Similarity	NPC268954
0.87	High Similarity	NPC40918
0.87	High Similarity	NPC476890
0.8687	High Similarity	NPC476195
0.8679	High Similarity	NPC110861
0.8611	High Similarity	NPC470515
0.8602	High Similarity	NPC137306
0.8602	High Similarity	NPC84121
0.86	High Similarity	NPC476132
0.86	High Similarity	NPC476888
0.86	High Similarity	NPC93744
0.8598	High Similarity	NPC44170
0.8586	High Similarity	NPC477876
0.8586	High Similarity	NPC477875
0.8571	High Similarity	NPC230151
0.8571	High Similarity	NPC88009
0.8557	High Similarity	NPC296164
0.8557	High Similarity	NPC215700
0.8557	High Similarity	NPC91010
0.8532	High Similarity	NPC470914
0.8532	High Similarity	NPC470911
0.8532	High Similarity	NPC470517
0.8532	High Similarity	NPC470915
0.85	High Similarity	NPC473510
0.85	High Similarity	NPC230546
0.8495	Intermediate Similarity	NPC191965
0.8485	Intermediate Similarity	NPC210337
0.8485	Intermediate Similarity	NPC51499
0.8454	Intermediate Similarity	NPC86368
0.8416	Intermediate Similarity	NPC233012
0.8416	Intermediate Similarity	NPC54909
0.8411	Intermediate Similarity	NPC473159
0.84	Intermediate Similarity	NPC247233
0.84	Intermediate Similarity	NPC275086
0.84	Intermediate Similarity	NPC325229
0.8367	Intermediate Similarity	NPC20235
0.8367	Intermediate Similarity	NPC263548
0.8367	Intermediate Similarity	NPC88116
0.8367	Intermediate Similarity	NPC32407
0.8367	Intermediate Similarity	NPC231063
0.8367	Intermediate Similarity	NPC145667
0.8367	Intermediate Similarity	NPC299996
0.8367	Intermediate Similarity	NPC74751
0.8367	Intermediate Similarity	NPC282395
0.8333	Intermediate Similarity	NPC475344
0.8333	Intermediate Similarity	NPC476471
0.8333	Intermediate Similarity	NPC82876
0.8317	Intermediate Similarity	NPC474571
0.8317	Intermediate Similarity	NPC254567
0.83	Intermediate Similarity	NPC73911
0.83	Intermediate Similarity	NPC26413
0.8286	Intermediate Similarity	NPC473483
0.8286	Intermediate Similarity	NPC88701
0.8269	Intermediate Similarity	NPC477877
0.8265	Intermediate Similarity	NPC214756
0.8265	Intermediate Similarity	NPC53555
0.8265	Intermediate Similarity	NPC74855
0.8265	Intermediate Similarity	NPC169343
0.8265	Intermediate Similarity	NPC38232
0.8265	Intermediate Similarity	NPC295643
0.8265	Intermediate Similarity	NPC136313
0.8265	Intermediate Similarity	NPC307335
0.8265	Intermediate Similarity	NPC272075
0.8252	Intermediate Similarity	NPC281378
0.8252	Intermediate Similarity	NPC473523
0.8252	Intermediate Similarity	NPC474124
0.8247	Intermediate Similarity	NPC120840
0.8247	Intermediate Similarity	NPC113989
0.8247	Intermediate Similarity	NPC130278
0.8247	Intermediate Similarity	NPC78973
0.8235	Intermediate Similarity	NPC475617
0.8235	Intermediate Similarity	NPC235142
0.8218	Intermediate Similarity	NPC471966
0.8218	Intermediate Similarity	NPC92275
0.8211	Intermediate Similarity	NPC131813
0.8208	Intermediate Similarity	NPC310546
0.8208	Intermediate Similarity	NPC475586
0.82	Intermediate Similarity	NPC25848
0.82	Intermediate Similarity	NPC19376
0.82	Intermediate Similarity	NPC201657
0.82	Intermediate Similarity	NPC204961
0.82	Intermediate Similarity	NPC305464
0.82	Intermediate Similarity	NPC327179
0.82	Intermediate Similarity	NPC73004
0.82	Intermediate Similarity	NPC173744
0.82	Intermediate Similarity	NPC98874
0.82	Intermediate Similarity	NPC307282
0.8198	Intermediate Similarity	NPC211093
0.8198	Intermediate Similarity	NPC77689
0.8198	Intermediate Similarity	NPC473636
0.8198	Intermediate Similarity	NPC473839
0.819	Intermediate Similarity	NPC475570
0.819	Intermediate Similarity	NPC301666
0.819	Intermediate Similarity	NPC471205
0.8182	Intermediate Similarity	NPC78580
0.8182	Intermediate Similarity	NPC184006
0.8182	Intermediate Similarity	NPC473405
0.8182	Intermediate Similarity	NPC23621
0.8173	Intermediate Similarity	NPC473543
0.8172	Intermediate Similarity	NPC304285
0.8172	Intermediate Similarity	NPC286786
0.8163	Intermediate Similarity	NPC4036
0.8163	Intermediate Similarity	NPC306541
0.8163	Intermediate Similarity	NPC60755
0.8163	Intermediate Similarity	NPC71074
0.8163	Intermediate Similarity	NPC233455
0.8163	Intermediate Similarity	NPC41239
0.8163	Intermediate Similarity	NPC72845
0.8163	Intermediate Similarity	NPC472149
0.8163	Intermediate Similarity	NPC285184
0.8163	Intermediate Similarity	NPC300351
0.8163	Intermediate Similarity	NPC77099
0.8163	Intermediate Similarity	NPC470590
0.8163	Intermediate Similarity	NPC25299
0.8163	Intermediate Similarity	NPC65120
0.8163	Intermediate Similarity	NPC84319
0.8163	Intermediate Similarity	NPC145067
0.8163	Intermediate Similarity	NPC158030
0.8163	Intermediate Similarity	NPC235884
0.8163	Intermediate Similarity	NPC329842
0.8163	Intermediate Similarity	NPC52021
0.8155	Intermediate Similarity	NPC472552
0.8144	Intermediate Similarity	NPC121798
0.8144	Intermediate Similarity	NPC263393
0.8144	Intermediate Similarity	NPC30522
0.8144	Intermediate Similarity	NPC130520
0.8144	Intermediate Similarity	NPC290972
0.8144	Intermediate Similarity	NPC234346
0.8144	Intermediate Similarity	NPC25906
0.8144	Intermediate Similarity	NPC293048
0.8144	Intermediate Similarity	NPC225585
0.8144	Intermediate Similarity	NPC59263
0.8144	Intermediate Similarity	NPC270768
0.8144	Intermediate Similarity	NPC64872
0.8144	Intermediate Similarity	NPC127689
0.8144	Intermediate Similarity	NPC61543
0.8137	Intermediate Similarity	NPC38855
0.8119	Intermediate Similarity	NPC247139
0.8119	Intermediate Similarity	NPC476878
0.8119	Intermediate Similarity	NPC151681
0.8119	Intermediate Similarity	NPC9613
0.8119	Intermediate Similarity	NPC261935
0.8119	Intermediate Similarity	NPC476879
0.8119	Intermediate Similarity	NPC121402
0.8119	Intermediate Similarity	NPC175351
0.8119	Intermediate Similarity	NPC106112
0.8119	Intermediate Similarity	NPC132753
0.8119	Intermediate Similarity	NPC224356
0.8119	Intermediate Similarity	NPC255589
0.8119	Intermediate Similarity	NPC259788
0.8113	Intermediate Similarity	NPC189075
0.8113	Intermediate Similarity	NPC275539
0.8108	Intermediate Similarity	NPC471548
0.8105	Intermediate Similarity	NPC35933
0.8105	Intermediate Similarity	NPC474013
0.81	Intermediate Similarity	NPC23241
0.81	Intermediate Similarity	NPC474727
0.81	Intermediate Similarity	NPC148523
0.81	Intermediate Similarity	NPC195715
0.81	Intermediate Similarity	NPC139570
0.81	Intermediate Similarity	NPC32118
0.81	Intermediate Similarity	NPC276110
0.81	Intermediate Similarity	NPC96916
0.8095	Intermediate Similarity	NPC51719
0.8095	Intermediate Similarity	NPC471206
0.8085	Intermediate Similarity	NPC253402
0.8085	Intermediate Similarity	NPC132386
0.8085	Intermediate Similarity	NPC159168
0.8081	Intermediate Similarity	NPC205034
0.8081	Intermediate Similarity	NPC152778
0.8081	Intermediate Similarity	NPC162615
0.8081	Intermediate Similarity	NPC275809
0.8081	Intermediate Similarity	NPC229281
0.8081	Intermediate Similarity	NPC139692
0.8077	Intermediate Similarity	NPC112009
0.8077	Intermediate Similarity	NPC478057
0.8077	Intermediate Similarity	NPC473124
0.8077	Intermediate Similarity	NPC473123
0.8077	Intermediate Similarity	NPC180204
0.8065	Intermediate Similarity	NPC195334
0.8065	Intermediate Similarity	NPC290495
0.8061	Intermediate Similarity	NPC210037
0.8061	Intermediate Similarity	NPC290614
0.8061	Intermediate Similarity	NPC7260
0.8061	Intermediate Similarity	NPC227467
0.8061	Intermediate Similarity	NPC198818
0.8061	Intermediate Similarity	NPC273621
0.8061	Intermediate Similarity	NPC474728
0.8061	Intermediate Similarity	NPC92885
0.8061	Intermediate Similarity	NPC126369

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 NPC473160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1617
0.2-0.3	3815
0.3-0.4	2330
0.4-0.5	759
0.5-0.6	236
0.6-0.7	160
0.7-0.8	30
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
0.8367	Intermediate Similarity	NPD7748	Approved
0.83	Intermediate Similarity	NPD7902	Approved
0.8163	Intermediate Similarity	NPD7515	Phase 2
0.8039	Intermediate Similarity	NPD4225	Approved
0.8039	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD7900	Approved
0.8	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD7640	Approved
0.7961	Intermediate Similarity	NPD7639	Approved
0.7849	Intermediate Similarity	NPD7645	Phase 2
0.7699	Intermediate Similarity	NPD7115	Discovery
0.7652	Intermediate Similarity	NPD8377	Approved
0.7652	Intermediate Similarity	NPD8294	Approved
0.7586	Intermediate Similarity	NPD8378	Approved
0.7586	Intermediate Similarity	NPD8033	Approved
0.7586	Intermediate Similarity	NPD8296	Approved
0.7586	Intermediate Similarity	NPD8379	Approved
0.7586	Intermediate Similarity	NPD8335	Approved
0.7586	Intermediate Similarity	NPD8380	Approved
0.7565	Intermediate Similarity	NPD7516	Approved
0.7545	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8297	Approved
0.7478	Intermediate Similarity	NPD7328	Approved
0.7478	Intermediate Similarity	NPD7327	Approved
0.7455	Intermediate Similarity	NPD6686	Approved
0.7436	Intermediate Similarity	NPD7503	Approved
0.7383	Intermediate Similarity	NPD5344	Discontinued
0.7321	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7632	Discontinued
0.7311	Intermediate Similarity	NPD8328	Phase 3
0.7297	Intermediate Similarity	NPD6899	Approved
0.7297	Intermediate Similarity	NPD6881	Approved
0.7282	Intermediate Similarity	NPD8035	Phase 2
0.7282	Intermediate Similarity	NPD8034	Phase 2
0.7273	Intermediate Similarity	NPD5739	Approved
0.7273	Intermediate Similarity	NPD7128	Approved
0.7273	Intermediate Similarity	NPD6675	Approved
0.7273	Intermediate Similarity	NPD6402	Approved
0.7257	Intermediate Similarity	NPD8130	Phase 1
0.7232	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5697	Approved
0.719	Intermediate Similarity	NPD7507	Approved
0.7168	Intermediate Similarity	NPD7102	Approved
0.7168	Intermediate Similarity	NPD7290	Approved
0.7168	Intermediate Similarity	NPD6883	Approved
0.7143	Intermediate Similarity	NPD7320	Approved
0.713	Intermediate Similarity	NPD6648	Approved
0.7105	Intermediate Similarity	NPD6617	Approved
0.7105	Intermediate Similarity	NPD6847	Approved
0.7105	Intermediate Similarity	NPD6649	Approved
0.7105	Intermediate Similarity	NPD6869	Approved
0.7105	Intermediate Similarity	NPD6650	Approved
0.708	Intermediate Similarity	NPD6373	Approved
0.708	Intermediate Similarity	NPD6372	Approved
0.708	Intermediate Similarity	NPD6013	Approved
0.708	Intermediate Similarity	NPD6012	Approved
0.708	Intermediate Similarity	NPD6014	Approved
0.7071	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5701	Approved
0.7054	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6399	Phase 3
0.7043	Intermediate Similarity	NPD6882	Approved
0.7041	Intermediate Similarity	NPD7525	Registered
0.703	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7838	Discovery
0.7016	Intermediate Similarity	NPD7319	Approved
0.6991	Remote Similarity	NPD6011	Approved
0.699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8133	Approved
0.6961	Remote Similarity	NPD3618	Phase 1
0.6952	Remote Similarity	NPD6079	Approved
0.6949	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6084	Phase 2
0.6944	Remote Similarity	NPD6083	Phase 2
0.6935	Remote Similarity	NPD7736	Approved
0.6923	Remote Similarity	NPD6051	Approved
0.6923	Remote Similarity	NPD5328	Approved
0.6903	Remote Similarity	NPD6412	Phase 2
0.6893	Remote Similarity	NPD3573	Approved
0.6863	Remote Similarity	NPD1694	Approved
0.6847	Remote Similarity	NPD5211	Phase 2
0.6842	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4632	Approved
0.6818	Remote Similarity	NPD4696	Approved
0.6818	Remote Similarity	NPD5285	Approved
0.6818	Remote Similarity	NPD5286	Approved
0.681	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7521	Approved
0.6796	Remote Similarity	NPD6409	Approved
0.6796	Remote Similarity	NPD7334	Approved
0.6796	Remote Similarity	NPD7146	Approved
0.6796	Remote Similarity	NPD6684	Approved
0.6796	Remote Similarity	NPD5330	Approved
0.6789	Remote Similarity	NPD4755	Approved
0.6777	Remote Similarity	NPD6319	Approved
0.6765	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD4202	Approved
0.6726	Remote Similarity	NPD5141	Approved
0.6723	Remote Similarity	NPD6274	Approved
0.6698	Remote Similarity	NPD6698	Approved
0.6698	Remote Similarity	NPD46	Approved
0.6697	Remote Similarity	NPD5221	Approved
0.6697	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5222	Approved
0.6696	Remote Similarity	NPD5224	Approved
0.6696	Remote Similarity	NPD5225	Approved
0.6696	Remote Similarity	NPD5226	Approved
0.6696	Remote Similarity	NPD4633	Approved
0.6694	Remote Similarity	NPD7100	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6694	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.664	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6637	Remote Similarity	NPD5174	Approved
0.6637	Remote Similarity	NPD5175	Approved
0.6636	Remote Similarity	NPD5173	Approved
0.6636	Remote Similarity	NPD6411	Approved
0.6613	Remote Similarity	NPD7604	Phase 2
0.6612	Remote Similarity	NPD6335	Approved
0.6607	Remote Similarity	NPD5223	Approved
0.6606	Remote Similarity	NPD5695	Phase 3
0.6602	Remote Similarity	NPD3133	Approved
0.6602	Remote Similarity	NPD3666	Approved
0.6602	Remote Similarity	NPD3665	Phase 1
0.6602	Remote Similarity	NPD4786	Approved
0.6587	Remote Similarity	NPD7078	Approved
0.6587	Remote Similarity	NPD8293	Discontinued
0.6585	Remote Similarity	NPD5983	Phase 2
0.6583	Remote Similarity	NPD6868	Approved
0.6577	Remote Similarity	NPD5696	Approved
0.6577	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3667	Approved
0.6545	Remote Similarity	NPD7732	Phase 3
0.6545	Remote Similarity	NPD4697	Phase 3
0.6545	Remote Similarity	NPD7614	Phase 1
0.6532	Remote Similarity	NPD6370	Approved
0.6531	Remote Similarity	NPD7339	Approved
0.6531	Remote Similarity	NPD6942	Approved
0.6529	Remote Similarity	NPD6317	Approved
0.6508	Remote Similarity	NPD6336	Discontinued
0.6504	Remote Similarity	NPD6059	Approved
0.6481	Remote Similarity	NPD5693	Phase 1
0.6481	Remote Similarity	NPD7637	Suspended
0.6475	Remote Similarity	NPD6314	Approved
0.6475	Remote Similarity	NPD6313	Approved
0.6471	Remote Similarity	NPD6053	Discontinued
0.6465	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4159	Approved
0.6455	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8515	Approved
0.6452	Remote Similarity	NPD6908	Approved
0.6452	Remote Similarity	NPD8513	Phase 3
0.6452	Remote Similarity	NPD8516	Approved
0.6452	Remote Similarity	NPD8517	Approved
0.6452	Remote Similarity	NPD6016	Approved
0.6452	Remote Similarity	NPD6015	Approved
0.6452	Remote Similarity	NPD6909	Approved
0.6449	Remote Similarity	NPD4753	Phase 2
0.6449	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6101	Approved
0.6441	Remote Similarity	NPD4634	Approved
0.6422	Remote Similarity	NPD5779	Approved
0.6422	Remote Similarity	NPD5778	Approved
0.6415	Remote Similarity	NPD7524	Approved
0.641	Remote Similarity	NPD4729	Approved
0.641	Remote Similarity	NPD4730	Approved
0.641	Remote Similarity	NPD5128	Approved
0.64	Remote Similarity	NPD5988	Approved
0.6379	Remote Similarity	NPD4767	Approved
0.6379	Remote Similarity	NPD6008	Approved
0.6379	Remote Similarity	NPD4768	Approved
0.6373	Remote Similarity	NPD4695	Discontinued
0.6364	Remote Similarity	NPD8264	Approved
0.6348	Remote Similarity	NPD4754	Approved
0.6321	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4629	Approved
0.6306	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5210	Approved
0.6303	Remote Similarity	NPD5251	Approved
0.6303	Remote Similarity	NPD6371	Approved
0.6303	Remote Similarity	NPD5250	Approved
0.6303	Remote Similarity	NPD5248	Approved
0.6303	Remote Similarity	NPD5247	Approved
0.6303	Remote Similarity	NPD5249	Phase 3
0.6296	Remote Similarity	NPD6673	Approved
0.6296	Remote Similarity	NPD6080	Approved
0.6296	Remote Similarity	NPD6904	Approved
0.6286	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5290	Discontinued
0.6275	Remote Similarity	NPD4195	Approved
0.625	Remote Similarity	NPD5217	Approved
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5215	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