NPASS Compound

Structure

NPC472028 OpenBabel07101718222D 41 45 0 0 1 0 0 0 0 0999 V2000 5.7633 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1161 6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7852 5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4762 4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 2 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 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 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 2 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 31 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 27 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 17 1 0 0 0 0 16 31 1 0 0 0 0 17 34 1 0 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 22 4 1 1 0 0 0 22 25 1 0 0 0 0 23 36 2 0 0 0 0 23 40 1 0 0 0 0 24 37 2 0 0 0 0 24 41 1 0 0 0 0 25 31 1 1 0 0 0 26 32 1 6 0 0 0 26 34 1 0 0 0 0 27 33 1 1 0 0 0 27 35 1 0 0 0 0 28 33 1 1 0 0 0 28 40 1 0 0 0 0 29 35 1 6 0 0 0 29 41 1 0 0 0 0 30 33 1 0 0 0 0 30 38 2 0 0 0 0 30 39 1 0 0 0 0 31 32 1 1 0 0 0 32 8 1 6 0 0 0 33 9 1 1 0 0 0 34 35 1 6 0 0 0 35 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.39
Volume:	613.329
LogP:	6.545
LogD:	4.656
LogS:	-5.078
# Rotatable Bonds:	10
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.239
Synthetic Accessibility Score:	5.957
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:	-5.448
MDCK Permeability:	3.523692794260569e-05
Pgp-inhibitor:	0.525
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.879

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.442
Plasma Protein Binding (PPB):	90.52179718017578%
Volume Distribution (VD):	0.858
Pgp-substrate:	3.2432849407196045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.758
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.582
CYP3A4-substrate:	0.422

ADMET: Excretion

Clearance (CL):	2.31
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.536
Human Hepatotoxicity (H-HT):	0.373
Drug-inuced Liver Injury (DILI):	0.836
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.645
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.905
Carcinogencity:	0.467
Eye Corrosion:	0.256
Eye Irritation:	0.026
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC472028

Natural Product ID:	NPC472028
*Common Name:**	XXQZXARMTRVCHW-VSMYQFNNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XXQZXARMTRVCHW-VSMYQFNNSA-N
Standard InCHI:	InChI=1S/C35H54O6/c1-20(2)21(3)10-11-22(4)25-14-15-32(8)26-12-13-27-33(9,30(38)39)28(40-23(5)36)18-29(41-24(6)37)35(27)19-34(26,35)17-16-31(25,32)7/h20,22,25-29H,3,10-19H2,1-2,4-9H3,(H,38,39)/t22-,25-,26+,27+,28+,29+,31-,32+,33+,34+,35-/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@H](OC(=O)C)[C@@]([C@H]2[C@@]31C[C@@]13CC[C@]3([C@@]([C@@H]1CC2)(C)CC[C@@H]3[C@@H](CCC(=C)C(C)C)C)C)(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL333068
PubChem CID:	10769395
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	52.54	uM	PMID[513272]

☑ 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 NPC472028 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	229
0.1-0.2	1835
0.2-0.3	6119
0.3-0.4	12611
0.4-0.5	8651
0.5-0.6	5607
0.6-0.7	5581
0.7-0.8	1810
0.8-0.85	174
0.85-0.9	67
0.9-0.95	6
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC94906
0.9681	High Similarity	NPC124544
0.9574	High Similarity	NPC75941
0.9468	High Similarity	NPC37047
0.9468	High Similarity	NPC41971
0.9468	High Similarity	NPC180733
0.9462	High Similarity	NPC469810
0.9457	High Similarity	NPC263135
0.9457	High Similarity	NPC288906
0.9149	High Similarity	NPC234564
0.9043	High Similarity	NPC470229
0.8969	High Similarity	NPC46848
0.8969	High Similarity	NPC71706
0.8947	High Similarity	NPC327788
0.8947	High Similarity	NPC329910
0.8936	High Similarity	NPC475118
0.8925	High Similarity	NPC471901
0.8922	High Similarity	NPC270586
0.8878	High Similarity	NPC76866
0.8878	High Similarity	NPC88203
0.8878	High Similarity	NPC304832
0.8878	High Similarity	NPC246736
0.8878	High Similarity	NPC286519
0.8878	High Similarity	NPC214946
0.8878	High Similarity	NPC193934
0.8878	High Similarity	NPC275990
0.8878	High Similarity	NPC271980
0.8878	High Similarity	NPC148628
0.8854	High Similarity	NPC253586
0.8842	High Similarity	NPC266431
0.8842	High Similarity	NPC470232
0.883	High Similarity	NPC473690
0.883	High Similarity	NPC287118
0.883	High Similarity	NPC471902
0.8804	High Similarity	NPC146937
0.8788	High Similarity	NPC470310
0.8788	High Similarity	NPC312900
0.8776	High Similarity	NPC163963
0.8776	High Similarity	NPC289148
0.8776	High Similarity	NPC52899
0.8763	High Similarity	NPC119036
0.8763	High Similarity	NPC98837
0.8763	High Similarity	NPC28864
0.8763	High Similarity	NPC471038
0.8763	High Similarity	NPC474793
0.8763	High Similarity	NPC38296
0.8763	High Similarity	NPC38471
0.8763	High Similarity	NPC20479
0.8763	High Similarity	NPC162459
0.8737	High Similarity	NPC470386
0.8737	High Similarity	NPC470385
0.8737	High Similarity	NPC47853
0.8723	High Similarity	NPC475416
0.8723	High Similarity	NPC470230
0.8673	High Similarity	NPC108371
0.8673	High Similarity	NPC293866
0.8673	High Similarity	NPC287676
0.866	High Similarity	NPC190080
0.866	High Similarity	NPC111187
0.8627	High Similarity	NPC163216
0.8627	High Similarity	NPC211224
0.8614	High Similarity	NPC295366
0.8614	High Similarity	NPC200957
0.8614	High Similarity	NPC265127
0.8614	High Similarity	NPC138908
0.8614	High Similarity	NPC37600
0.8602	High Similarity	NPC4309
0.86	High Similarity	NPC87927
0.8587	High Similarity	NPC302111
0.8586	High Similarity	NPC236585
0.8586	High Similarity	NPC253886
0.8586	High Similarity	NPC121218
0.8571	High Similarity	NPC16911
0.8571	High Similarity	NPC89099
0.8571	High Similarity	NPC78427
0.8558	High Similarity	NPC470281
0.8557	High Similarity	NPC29410
0.8557	High Similarity	NPC200054
0.8557	High Similarity	NPC470387
0.8544	High Similarity	NPC285298
0.8544	High Similarity	NPC257082
0.8529	High Similarity	NPC201908
0.8529	High Similarity	NPC176949
0.8529	High Similarity	NPC166993
0.8529	High Similarity	NPC263729
0.8526	High Similarity	NPC211403
0.8526	High Similarity	NPC198242
0.8515	High Similarity	NPC98603
0.8515	High Similarity	NPC201763
0.8515	High Similarity	NPC84928
0.8511	High Similarity	NPC57954
0.8511	High Similarity	NPC213832
0.8511	High Similarity	NPC471043
0.85	High Similarity	NPC170615
0.8469	Intermediate Similarity	NPC10864
0.8462	Intermediate Similarity	NPC471037
0.8454	Intermediate Similarity	NPC279974
0.8454	Intermediate Similarity	NPC205173
0.8454	Intermediate Similarity	NPC98639
0.8447	Intermediate Similarity	NPC231278
0.8447	Intermediate Similarity	NPC218123
0.8447	Intermediate Similarity	NPC112895
0.8447	Intermediate Similarity	NPC273155
0.8438	Intermediate Similarity	NPC224060
0.8438	Intermediate Similarity	NPC294263
0.8438	Intermediate Similarity	NPC244356
0.8421	Intermediate Similarity	NPC10274
0.8416	Intermediate Similarity	NPC139347
0.8416	Intermediate Similarity	NPC122811
0.8416	Intermediate Similarity	NPC277074
0.8416	Intermediate Similarity	NPC469985
0.8416	Intermediate Similarity	NPC209298
0.8416	Intermediate Similarity	NPC216114
0.8404	Intermediate Similarity	NPC471900
0.84	Intermediate Similarity	NPC471790
0.84	Intermediate Similarity	NPC289670
0.84	Intermediate Similarity	NPC295276
0.837	Intermediate Similarity	NPC299963
0.837	Intermediate Similarity	NPC319909
0.8367	Intermediate Similarity	NPC13949
0.8351	Intermediate Similarity	NPC469982
0.8333	Intermediate Similarity	NPC47281
0.8333	Intermediate Similarity	NPC250753
0.8333	Intermediate Similarity	NPC301787
0.8333	Intermediate Similarity	NPC160506
0.8317	Intermediate Similarity	NPC473788
0.8317	Intermediate Similarity	NPC475558
0.8316	Intermediate Similarity	NPC24705
0.8316	Intermediate Similarity	NPC56962
0.8302	Intermediate Similarity	NPC476964
0.83	Intermediate Similarity	NPC470388
0.8298	Intermediate Similarity	NPC264005
0.8298	Intermediate Similarity	NPC134197
0.8298	Intermediate Similarity	NPC33768
0.8298	Intermediate Similarity	NPC269360
0.8283	Intermediate Similarity	NPC170978
0.828	Intermediate Similarity	NPC98270
0.8265	Intermediate Similarity	NPC210214
0.8252	Intermediate Similarity	NPC4115
0.8252	Intermediate Similarity	NPC278628
0.8252	Intermediate Similarity	NPC28791
0.8252	Intermediate Similarity	NPC50535
0.8252	Intermediate Similarity	NPC231530
0.8252	Intermediate Similarity	NPC222833
0.8247	Intermediate Similarity	NPC477855
0.8247	Intermediate Similarity	NPC475061
0.8235	Intermediate Similarity	NPC222153
0.8235	Intermediate Similarity	NPC96217
0.8229	Intermediate Similarity	NPC169933
0.8229	Intermediate Similarity	NPC471896
0.8224	Intermediate Similarity	NPC73986
0.8218	Intermediate Similarity	NPC148279
0.8218	Intermediate Similarity	NPC252614
0.8218	Intermediate Similarity	NPC39683
0.8208	Intermediate Similarity	NPC94650
0.8208	Intermediate Similarity	NPC470311
0.82	Intermediate Similarity	NPC102426
0.82	Intermediate Similarity	NPC300179
0.8191	Intermediate Similarity	NPC12774
0.8191	Intermediate Similarity	NPC2783
0.819	Intermediate Similarity	NPC16657
0.819	Intermediate Similarity	NPC204652
0.8182	Intermediate Similarity	NPC120708
0.8173	Intermediate Similarity	NPC86852
0.8173	Intermediate Similarity	NPC251824
0.8173	Intermediate Similarity	NPC61071
0.8172	Intermediate Similarity	NPC471044
0.8172	Intermediate Similarity	NPC473336
0.8172	Intermediate Similarity	NPC475509
0.8163	Intermediate Similarity	NPC277399
0.8163	Intermediate Similarity	NPC261333
0.8163	Intermediate Similarity	NPC292374
0.8163	Intermediate Similarity	NPC215271
0.8163	Intermediate Similarity	NPC29247
0.8163	Intermediate Similarity	NPC104371
0.8163	Intermediate Similarity	NPC129004
0.8163	Intermediate Similarity	NPC101233
0.8163	Intermediate Similarity	NPC289539
0.8163	Intermediate Similarity	NPC303863
0.8163	Intermediate Similarity	NPC153775
0.8163	Intermediate Similarity	NPC91772
0.8163	Intermediate Similarity	NPC111524
0.8155	Intermediate Similarity	NPC310586
0.8155	Intermediate Similarity	NPC202793
0.8155	Intermediate Similarity	NPC328737
0.8155	Intermediate Similarity	NPC474558
0.8152	Intermediate Similarity	NPC472504
0.8144	Intermediate Similarity	NPC219516
0.8144	Intermediate Similarity	NPC476934
0.8137	Intermediate Similarity	NPC15396
0.8137	Intermediate Similarity	NPC475803
0.8137	Intermediate Similarity	NPC309388
0.8125	Intermediate Similarity	NPC474889
0.8119	Intermediate Similarity	NPC267921
0.8119	Intermediate Similarity	NPC477656
0.8119	Intermediate Similarity	NPC293890
0.8105	Intermediate Similarity	NPC259009
0.8105	Intermediate Similarity	NPC57469
0.81	Intermediate Similarity	NPC476878
0.81	Intermediate Similarity	NPC476879

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 NPC472028 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	2240
0.2-0.3	4031
0.3-0.4	1760
0.4-0.5	419
0.5-0.6	241
0.6-0.7	190
0.7-0.8	52
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD8034	Phase 2
0.8333	Intermediate Similarity	NPD8035	Phase 2
0.8085	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6697	Approved
0.7717	Intermediate Similarity	NPD6118	Approved
0.7717	Intermediate Similarity	NPD6115	Approved
0.7717	Intermediate Similarity	NPD6114	Approved
0.767	Intermediate Similarity	NPD7638	Approved
0.7596	Intermediate Similarity	NPD7639	Approved
0.7596	Intermediate Similarity	NPD7640	Approved
0.757	Intermediate Similarity	NPD7128	Approved
0.757	Intermediate Similarity	NPD6675	Approved
0.757	Intermediate Similarity	NPD5739	Approved
0.757	Intermediate Similarity	NPD6402	Approved
0.7525	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD6117	Approved
0.7451	Intermediate Similarity	NPD7748	Approved
0.7431	Intermediate Similarity	NPD6881	Approved
0.7431	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6899	Approved
0.7431	Intermediate Similarity	NPD7320	Approved
0.7419	Intermediate Similarity	NPD6116	Phase 1
0.7407	Intermediate Similarity	NPD6008	Approved
0.74	Intermediate Similarity	NPD5328	Approved
0.7387	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6372	Approved
0.7364	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD5701	Approved
0.7339	Intermediate Similarity	NPD5697	Approved
0.7333	Intermediate Similarity	NPD7736	Approved
0.7328	Intermediate Similarity	NPD6319	Approved
0.7321	Intermediate Similarity	NPD8297	Approved
0.7297	Intermediate Similarity	NPD7290	Approved
0.7297	Intermediate Similarity	NPD7102	Approved
0.7297	Intermediate Similarity	NPD6883	Approved
0.7283	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7319	Approved
0.7257	Intermediate Similarity	NPD8133	Approved
0.7255	Intermediate Similarity	NPD6079	Approved
0.725	Intermediate Similarity	NPD8293	Discontinued
0.7238	Intermediate Similarity	NPD7902	Approved
0.7232	Intermediate Similarity	NPD6617	Approved
0.7232	Intermediate Similarity	NPD6869	Approved
0.7232	Intermediate Similarity	NPD6650	Approved
0.7232	Intermediate Similarity	NPD6847	Approved
0.7232	Intermediate Similarity	NPD6649	Approved
0.7227	Intermediate Similarity	NPD7492	Approved
0.7207	Intermediate Similarity	NPD6013	Approved
0.7207	Intermediate Similarity	NPD6012	Approved
0.7207	Intermediate Similarity	NPD6014	Approved
0.7204	Intermediate Similarity	NPD3703	Phase 2
0.7179	Intermediate Similarity	NPD6059	Approved
0.7179	Intermediate Similarity	NPD6054	Approved
0.7168	Intermediate Similarity	NPD6882	Approved
0.7167	Intermediate Similarity	NPD6616	Approved
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.713	Intermediate Similarity	NPD7632	Discontinued
0.7117	Intermediate Similarity	NPD6011	Approved
0.7107	Intermediate Similarity	NPD7078	Approved
0.7105	Intermediate Similarity	NPD4632	Approved
0.7087	Intermediate Similarity	NPD7637	Suspended
0.7087	Intermediate Similarity	NPD7515	Phase 2
0.7087	Intermediate Similarity	NPD6411	Approved
0.708	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD6083	Phase 2
0.7075	Intermediate Similarity	NPD4755	Approved
0.7071	Intermediate Similarity	NPD4786	Approved
0.7069	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD6370	Approved
0.7048	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD8328	Phase 3
0.6991	Remote Similarity	NPD4634	Approved
0.6981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4697	Phase 3
0.6981	Remote Similarity	NPD5221	Approved
0.6981	Remote Similarity	NPD5222	Approved
0.6975	Remote Similarity	NPD6016	Approved
0.6975	Remote Similarity	NPD6015	Approved
0.697	Remote Similarity	NPD4788	Approved
0.6961	Remote Similarity	NPD5737	Approved
0.6961	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6672	Approved
0.6952	Remote Similarity	NPD7900	Approved
0.6952	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4700	Approved
0.6944	Remote Similarity	NPD4696	Approved
0.6944	Remote Similarity	NPD5285	Approved
0.6944	Remote Similarity	NPD5286	Approved
0.6931	Remote Similarity	NPD7521	Approved
0.6931	Remote Similarity	NPD6409	Approved
0.6931	Remote Similarity	NPD3618	Phase 1
0.6931	Remote Similarity	NPD7334	Approved
0.6931	Remote Similarity	NPD6684	Approved
0.6931	Remote Similarity	NPD7146	Approved
0.6931	Remote Similarity	NPD5330	Approved
0.6923	Remote Similarity	NPD6009	Approved
0.6917	Remote Similarity	NPD5988	Approved
0.6916	Remote Similarity	NPD5173	Approved
0.6903	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6101	Approved
0.6887	Remote Similarity	NPD5695	Phase 3
0.6882	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD1700	Approved
0.6869	Remote Similarity	NPD3667	Approved
0.6857	Remote Similarity	NPD5778	Approved
0.6857	Remote Similarity	NPD5779	Approved
0.6852	Remote Similarity	NPD5696	Approved
0.6842	Remote Similarity	NPD3702	Approved
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6274	Approved
0.6838	Remote Similarity	NPD6868	Approved
0.6837	Remote Similarity	NPD7525	Registered
0.6833	Remote Similarity	NPD5983	Phase 2
0.6818	Remote Similarity	NPD5211	Phase 2
0.6818	Remote Similarity	NPD5224	Approved
0.6818	Remote Similarity	NPD5225	Approved
0.6818	Remote Similarity	NPD5226	Approved
0.6818	Remote Similarity	NPD4633	Approved
0.6807	Remote Similarity	NPD7101	Approved
0.6807	Remote Similarity	NPD7100	Approved
0.6796	Remote Similarity	NPD6903	Approved
0.6757	Remote Similarity	NPD5174	Approved
0.6757	Remote Similarity	NPD5175	Approved
0.6754	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6336	Discontinued
0.6727	Remote Similarity	NPD5223	Approved
0.6726	Remote Similarity	NPD6412	Phase 2
0.6723	Remote Similarity	NPD6335	Approved
0.6702	Remote Similarity	NPD6081	Approved
0.6702	Remote Similarity	NPD5777	Approved
0.6698	Remote Similarity	NPD4202	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6696	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6909	Approved
0.6694	Remote Similarity	NPD6908	Approved
0.6694	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6033	Approved
0.6639	Remote Similarity	NPD6317	Approved
0.6637	Remote Similarity	NPD4768	Approved
0.6637	Remote Similarity	NPD4767	Approved
0.6636	Remote Similarity	NPD6001	Approved
0.6607	Remote Similarity	NPD4754	Approved
0.6602	Remote Similarity	NPD6098	Approved
0.6602	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7327	Approved
0.6583	Remote Similarity	NPD6314	Approved
0.6583	Remote Similarity	NPD7328	Approved
0.6583	Remote Similarity	NPD6313	Approved
0.6581	Remote Similarity	NPD6053	Discontinued
0.6579	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6904	Approved
0.6571	Remote Similarity	NPD6673	Approved
0.6571	Remote Similarity	NPD6080	Approved
0.6571	Remote Similarity	NPD4753	Phase 2
0.6569	Remote Similarity	NPD3133	Approved
0.6569	Remote Similarity	NPD3666	Approved
0.6569	Remote Similarity	NPD3668	Phase 3
0.6569	Remote Similarity	NPD3665	Phase 1
0.6559	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5360	Phase 3
0.6557	Remote Similarity	NPD8380	Approved
0.6557	Remote Similarity	NPD8335	Approved
0.6557	Remote Similarity	NPD8379	Approved
0.6557	Remote Similarity	NPD8378	Approved
0.6557	Remote Similarity	NPD8296	Approved
0.6545	Remote Similarity	NPD4225	Approved
0.6538	Remote Similarity	NPD3573	Approved
0.6529	Remote Similarity	NPD7516	Approved
0.6522	Remote Similarity	NPD4730	Approved
0.6522	Remote Similarity	NPD5128	Approved
0.6522	Remote Similarity	NPD6686	Approved
0.6522	Remote Similarity	NPD4729	Approved
0.6522	Remote Similarity	NPD4224	Phase 2
0.6486	Remote Similarity	NPD8418	Phase 2
0.6475	Remote Similarity	NPD8294	Approved
0.6475	Remote Similarity	NPD8377	Approved
0.6471	Remote Similarity	NPD6695	Phase 3
0.6423	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8033	Approved
0.6421	Remote Similarity	NPD4244	Approved
0.6421	Remote Similarity	NPD4789	Approved
0.6421	Remote Similarity	NPD4245	Approved
0.641	Remote Similarity	NPD5247	Approved
0.641	Remote Similarity	NPD5249	Phase 3
0.641	Remote Similarity	NPD5248	Approved
0.641	Remote Similarity	NPD5250	Approved
0.641	Remote Similarity	NPD5251	Approved
0.6408	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7645	Phase 2
0.6381	Remote Similarity	NPD7750	Discontinued
0.6379	Remote Similarity	NPD5168	Approved
0.6373	Remote Similarity	NPD4223	Phase 3
0.6373	Remote Similarity	NPD4221	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