NPASS Compound

Structure

CID19862 OpenBabel06191715342D 42 46 0 0 1 0 0 0 0 0999 V2000 -4.0294 6.4338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5834 5.7414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2298 4.6393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8300 3.7421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5554 2.4926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7951 3.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7839 3.9469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3841 3.0497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8092 0.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9486 -0.4617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8512 -1.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7029 -0.9838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2571 1.4731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2568 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6046 1.7642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2184 -1.1196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7020 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8520 1.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 0.4919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7037 1.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4742 1.1574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8514 -1.4747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6065 5.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2067 4.7417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4071 2.9473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7440 0.4995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7022 -0.9828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7032 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4069 1.9650 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5549 0.4909 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8517 0.4914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3348 2.4220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2696 2.1186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2837 -0.8161 0.0000 C 0 0 0 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 -2.5552 1.4736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1302 3.3833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0791 0.1451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9997 2.7764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5535 -1.4739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 7 41 1 0 0 0 0 8 9 1 0 0 0 0 8 25 1 0 0 0 0 9 26 1 0 0 0 0 10 16 2 0 0 0 0 10 27 1 0 0 0 0 11 17 2 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 28 1 0 0 0 0 14 15 1 0 0 0 0 14 31 1 0 0 0 0 15 32 1 0 0 0 0 16 34 1 0 0 0 0 17 36 1 0 0 0 0 18 20 1 0 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 19 33 1 0 0 0 0 20 37 1 0 0 0 0 21 38 1 0 0 0 0 22 27 2 0 0 0 0 22 35 1 0 0 0 0 23 28 1 0 0 0 0 23 29 1 0 0 0 0 24 25 1 0 0 0 0 25 3 1 6 0 0 0 26 4 1 1 0 0 0 26 31 1 0 0 0 0 28 37 1 6 0 0 0 29 42 1 6 0 0 0 30 13 1 1 0 0 0 30 32 1 0 0 0 0 30 33 1 0 0 0 0 31 38 1 6 0 0 0 32 38 1 6 0 0 0 33 37 1 6 0 0 0 34 35 2 0 0 0 0 34 39 1 0 0 0 0 35 41 1 0 0 0 0 36 40 2 0 0 0 0 36 42 1 0 0 0 0 37 5 1 6 0 0 0 38 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.43
Volume:	645.0
LogP:	9.555
LogD:	7.671
LogS:	-7.177
# Rotatable Bonds:	10
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.234
Synthetic Accessibility Score:	4.601
Fsp3:	0.763
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.9
MDCK Permeability:	2.1153940906515345e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.053
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	95.34351348876953%
Volume Distribution (VD):	2.37
Pgp-substrate:	2.4057533740997314%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.47
CYP2C19-inhibitor:	0.291
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.663
CYP2D6-inhibitor:	0.16
CYP2D6-substrate:	0.826
CYP3A4-inhibitor:	0.572
CYP3A4-substrate:	0.742

ADMET: Excretion

Clearance (CL):	7.927
Half-life (T1/2):	0.075

ADMET: Toxicity

hERG Blockers:	0.993
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.49
Skin Sensitization:	0.987
Carcinogencity:	0.056
Eye Corrosion:	0.646
Eye Irritation:	0.168
Respiratory Toxicity:	0.46

Download Data

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

Natural Product: NPC19862

Natural Product ID:	NPC19862
*Common Name:**	Campestanyl Ferulate
IUPAC Name:	[(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	NLHPCZDTMWKEFC-GTKUFFLCSA-N
Standard InCHI:	InChI=1S/C38H58O4/c1-24(2)25(3)8-9-26(4)31-14-15-32-30-13-12-28-23-29(18-20-37(28,5)33(30)19-21-38(31,32)6)42-36(40)17-11-27-10-16-34(39)35(22-27)41-7/h10-11,16-17,22,24-26,28-33,39H,8-9,12-15,18-21,23H2,1-7H3/b17-11+/t25-,26-,28+,29+,30+,31-,32+,33+,37+,38-/m1/s1
SMILES:	COc1cc(/C=C/C(=O)O[C@H]2CC[C@]3([C@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@H]2CC[C@@H]3[C@@H](CC[C@H](C(C)C)C)C)C)C)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3799176
PubChem CID:	13786591
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001691] Steroid esters

*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
NPO12126.1	Coix lacryma- jobi var. ma - yuen	Varieties	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Others	14

Activity Type	# Activity
Others	14

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.	K	=	0.018	/uM/s	PMID[553001]
NPT35	Others	n.a.	Activity	=	1.198	n.a.	PMID[553001]
NPT35	Others	n.a.	Activity	=	1.091	n.a.	PMID[553001]
NPT35	Others	n.a.	Activity	=	0.79	n.a.	PMID[553001]
NPT35	Others	n.a.	Activity	=	23.0	%	PMID[553001]
NPT35	Others	n.a.	Activity	=	27.0	%	PMID[553001]
NPT35	Others	n.a.	Activity	=	34.0	%	PMID[553001]
NPT35	Others	n.a.	Activity	=	43.0	%	PMID[553001]
NPT35	Others	n.a.	K	=	0.13	/min	PMID[553001]
NPT35	Others	n.a.	K	=	0.19	/min	PMID[553001]
NPT35	Others	n.a.	Activity	=	1.89	n.a.	PMID[553001]
NPT35	Others	n.a.	Activity	=	1.47	n.a.	PMID[553001]
NPT35	Others	n.a.	Activity	=	1.57	n.a.	PMID[553001]

☑ 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 NPC19862 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	327
0.1-0.2	1359
0.2-0.3	2814
0.3-0.4	5588
0.4-0.5	10732
0.5-0.6	9238
0.6-0.7	10122
0.7-0.8	2356
0.8-0.85	89
0.85-0.9	45
0.9-0.95	12
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC235195
0.9855	High Similarity	NPC280717
0.9855	High Similarity	NPC271607
0.9786	High Similarity	NPC96930
0.9786	High Similarity	NPC32017
0.9716	High Similarity	NPC298647
0.9716	High Similarity	NPC273358
0.9716	High Similarity	NPC292206
0.951	High Similarity	NPC470618
0.951	High Similarity	NPC145527
0.951	High Similarity	NPC208785
0.951	High Similarity	NPC470619
0.9448	High Similarity	NPC205392
0.9448	High Similarity	NPC105942
0.9433	High Similarity	NPC307205
0.9291	High Similarity	NPC252133
0.9286	High Similarity	NPC473612
0.9281	High Similarity	NPC76032
0.9281	High Similarity	NPC132723
0.922	High Similarity	NPC35212
0.9155	High Similarity	NPC310621
0.9091	High Similarity	NPC26045
0.9048	High Similarity	NPC118033
0.9021	High Similarity	NPC235557
0.8986	High Similarity	NPC475579
0.8986	High Similarity	NPC473773
0.8966	High Similarity	NPC66894
0.8966	High Similarity	NPC8102
0.8944	High Similarity	NPC110699
0.8944	High Similarity	NPC106055
0.8919	High Similarity	NPC473579
0.8919	High Similarity	NPC475454
0.8919	High Similarity	NPC473680
0.8919	High Similarity	NPC475311
0.8905	High Similarity	NPC30174
0.8873	High Similarity	NPC182249
0.8811	High Similarity	NPC271494
0.8811	High Similarity	NPC470616
0.8811	High Similarity	NPC155192
0.8811	High Similarity	NPC473591
0.8811	High Similarity	NPC470617
0.8782	High Similarity	NPC200726
0.8741	High Similarity	NPC139243
0.8741	High Similarity	NPC116742
0.8732	High Similarity	NPC120852
0.8732	High Similarity	NPC476699
0.8726	High Similarity	NPC286809
0.8726	High Similarity	NPC177362
0.8723	High Similarity	NPC11266
0.8671	High Similarity	NPC266545
0.8671	High Similarity	NPC202428
0.8633	High Similarity	NPC83062
0.863	High Similarity	NPC477873
0.863	High Similarity	NPC469447
0.8582	High Similarity	NPC321502
0.8571	High Similarity	NPC471876
0.8562	High Similarity	NPC67467
0.8553	High Similarity	NPC115203
0.8551	High Similarity	NPC213552
0.8551	High Similarity	NPC120225
0.8542	High Similarity	NPC471152
0.854	High Similarity	NPC60517
0.854	High Similarity	NPC20443
0.854	High Similarity	NPC146886
0.8514	High Similarity	NPC53520
0.8493	Intermediate Similarity	NPC29599
0.8483	Intermediate Similarity	NPC234548
0.8483	Intermediate Similarity	NPC248287
0.8478	Intermediate Similarity	NPC289459
0.8467	Intermediate Similarity	NPC252402
0.8467	Intermediate Similarity	NPC102934
0.8406	Intermediate Similarity	NPC246704
0.8403	Intermediate Similarity	NPC252343
0.8389	Intermediate Similarity	NPC473909
0.8389	Intermediate Similarity	NPC274960
0.8389	Intermediate Similarity	NPC143120
0.8369	Intermediate Similarity	NPC86257
0.8367	Intermediate Similarity	NPC304110
0.8367	Intermediate Similarity	NPC27518
0.8366	Intermediate Similarity	NPC478268
0.8345	Intermediate Similarity	NPC90431
0.8345	Intermediate Similarity	NPC29008
0.8345	Intermediate Similarity	NPC228771
0.8345	Intermediate Similarity	NPC266705
0.8333	Intermediate Similarity	NPC125495
0.8333	Intermediate Similarity	NPC67247
0.8333	Intermediate Similarity	NPC471942
0.8321	Intermediate Similarity	NPC70752
0.8311	Intermediate Similarity	NPC472410
0.8301	Intermediate Similarity	NPC178048
0.8299	Intermediate Similarity	NPC471875
0.8298	Intermediate Similarity	NPC478215
0.8298	Intermediate Similarity	NPC307050
0.8298	Intermediate Similarity	NPC277458
0.8288	Intermediate Similarity	NPC281780
0.8273	Intermediate Similarity	NPC265413
0.8273	Intermediate Similarity	NPC10154
0.8267	Intermediate Similarity	NPC163898
0.8264	Intermediate Similarity	NPC475468
0.8248	Intermediate Similarity	NPC204466
0.8239	Intermediate Similarity	NPC288290
0.8235	Intermediate Similarity	NPC261322
0.8231	Intermediate Similarity	NPC318575
0.8224	Intermediate Similarity	NPC95990
0.8219	Intermediate Similarity	NPC471988
0.8214	Intermediate Similarity	NPC9067
0.8207	Intermediate Similarity	NPC135127
0.8207	Intermediate Similarity	NPC176814
0.8207	Intermediate Similarity	NPC471110
0.8207	Intermediate Similarity	NPC68779
0.8207	Intermediate Similarity	NPC4982
0.8207	Intermediate Similarity	NPC5310
0.8207	Intermediate Similarity	NPC300776
0.8201	Intermediate Similarity	NPC317769
0.8201	Intermediate Similarity	NPC31344
0.82	Intermediate Similarity	NPC84684
0.82	Intermediate Similarity	NPC238216
0.82	Intermediate Similarity	NPC25491
0.82	Intermediate Similarity	NPC96447
0.82	Intermediate Similarity	NPC185388
0.82	Intermediate Similarity	NPC208994
0.8194	Intermediate Similarity	NPC475141
0.8194	Intermediate Similarity	NPC227002
0.8187	Intermediate Similarity	NPC100420
0.8175	Intermediate Similarity	NPC202474
0.817	Intermediate Similarity	NPC475250
0.8169	Intermediate Similarity	NPC201069
0.8169	Intermediate Similarity	NPC110313
0.8165	Intermediate Similarity	NPC478269
0.8163	Intermediate Similarity	NPC126206
0.816	Intermediate Similarity	NPC472803
0.8153	Intermediate Similarity	NPC11411
0.8151	Intermediate Similarity	NPC173569
0.8151	Intermediate Similarity	NPC43353
0.8151	Intermediate Similarity	NPC477874
0.8141	Intermediate Similarity	NPC473736
0.8141	Intermediate Similarity	NPC62051
0.8138	Intermediate Similarity	NPC227719
0.8129	Intermediate Similarity	NPC124842
0.8121	Intermediate Similarity	NPC82336
0.8121	Intermediate Similarity	NPC470372
0.8121	Intermediate Similarity	NPC78987
0.8116	Intermediate Similarity	NPC470848
0.8116	Intermediate Similarity	NPC470849
0.811	Intermediate Similarity	NPC469772
0.811	Intermediate Similarity	NPC469775
0.811	Intermediate Similarity	NPC100925
0.811	Intermediate Similarity	NPC469773
0.811	Intermediate Similarity	NPC295941
0.811	Intermediate Similarity	NPC469777
0.811	Intermediate Similarity	NPC32723
0.811	Intermediate Similarity	NPC469776
0.811	Intermediate Similarity	NPC469778
0.811	Intermediate Similarity	NPC135334
0.811	Intermediate Similarity	NPC469774
0.8105	Intermediate Similarity	NPC236166
0.8095	Intermediate Similarity	NPC471664
0.8095	Intermediate Similarity	NPC249817
0.8095	Intermediate Similarity	NPC68292
0.8095	Intermediate Similarity	NPC471665
0.8079	Intermediate Similarity	NPC209085
0.8079	Intermediate Similarity	NPC224884
0.8079	Intermediate Similarity	NPC471065
0.8079	Intermediate Similarity	NPC253015
0.8067	Intermediate Similarity	NPC476840
0.8067	Intermediate Similarity	NPC476842
0.8067	Intermediate Similarity	NPC131971
0.8065	Intermediate Similarity	NPC269914
0.8065	Intermediate Similarity	NPC478249
0.8063	Intermediate Similarity	NPC478267
0.8063	Intermediate Similarity	NPC149873
0.8063	Intermediate Similarity	NPC216916
0.8063	Intermediate Similarity	NPC7191
0.8052	Intermediate Similarity	NPC279442
0.8043	Intermediate Similarity	NPC117780
0.8043	Intermediate Similarity	NPC165133
0.8043	Intermediate Similarity	NPC2058
0.8043	Intermediate Similarity	NPC95614
0.8043	Intermediate Similarity	NPC242885
0.8043	Intermediate Similarity	NPC227217
0.8043	Intermediate Similarity	NPC232316
0.8043	Intermediate Similarity	NPC56214
0.8042	Intermediate Similarity	NPC129570
0.8042	Intermediate Similarity	NPC45774
0.8042	Intermediate Similarity	NPC128208
0.8042	Intermediate Similarity	NPC11258
0.8042	Intermediate Similarity	NPC282703
0.8042	Intermediate Similarity	NPC184733
0.8042	Intermediate Similarity	NPC21867
0.8041	Intermediate Similarity	NPC22676
0.8041	Intermediate Similarity	NPC216940
0.8041	Intermediate Similarity	NPC198621
0.8041	Intermediate Similarity	NPC475482
0.8039	Intermediate Similarity	NPC472938
0.8039	Intermediate Similarity	NPC472937
0.8039	Intermediate Similarity	NPC472936
0.8038	Intermediate Similarity	NPC478248
0.8037	Intermediate Similarity	NPC208818
0.8029	Intermediate Similarity	NPC272471
0.8029	Intermediate Similarity	NPC137537

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 NPC19862 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	845
0.2-0.3	1514
0.3-0.4	2588
0.4-0.5	2214
0.5-0.6	1217
0.6-0.7	447
0.7-0.8	51
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8582	High Similarity	NPD3620	Phase 2
0.8582	High Similarity	NPD3619	Clinical (unspecified phase)
0.8562	High Similarity	NPD8166	Discontinued
0.8526	High Similarity	NPD8127	Discontinued
0.8194	Intermediate Similarity	NPD4140	Approved
0.8039	Intermediate Similarity	NPD6273	Approved
0.7972	Intermediate Similarity	NPD5736	Approved
0.7947	Intermediate Similarity	NPD4110	Phase 3
0.7947	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD5735	Approved
0.7867	Intermediate Similarity	NPD5762	Approved
0.7867	Intermediate Similarity	NPD5763	Approved
0.7834	Intermediate Similarity	NPD7028	Phase 2
0.7823	Intermediate Similarity	NPD4060	Phase 1
0.7817	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD5327	Phase 3
0.777	Intermediate Similarity	NPD3657	Discovery
0.7765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7831	Phase 2
0.7764	Intermediate Similarity	NPD7833	Phase 2
0.7764	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6663	Approved
0.7755	Intermediate Similarity	NPD8032	Phase 2
0.774	Intermediate Similarity	NPD7095	Approved
0.7718	Intermediate Similarity	NPD6353	Approved
0.7655	Intermediate Similarity	NPD4624	Approved
0.7632	Intermediate Similarity	NPD7266	Discontinued
0.7607	Intermediate Similarity	NPD6234	Discontinued
0.7552	Intermediate Similarity	NPD3092	Approved
0.7547	Intermediate Similarity	NPD7458	Discontinued
0.7536	Intermediate Similarity	NPD5283	Phase 1
0.7535	Intermediate Similarity	NPD4626	Approved
0.7533	Intermediate Similarity	NPD6355	Discontinued
0.7529	Intermediate Similarity	NPD7685	Pre-registration
0.7518	Intermediate Similarity	NPD228	Approved
0.7518	Intermediate Similarity	NPD3091	Approved
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD7228	Approved
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7484	Intermediate Similarity	NPD7003	Approved
0.7466	Intermediate Similarity	NPD3094	Phase 2
0.7465	Intermediate Similarity	NPD5691	Approved
0.7452	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7097	Phase 1
0.7429	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6674	Discontinued
0.7407	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4966	Approved
0.7378	Intermediate Similarity	NPD4967	Phase 2
0.7378	Intermediate Similarity	NPD4965	Approved
0.7368	Intermediate Similarity	NPD6653	Approved
0.7343	Intermediate Similarity	NPD1357	Approved
0.7324	Intermediate Similarity	NPD5536	Phase 2
0.7305	Intermediate Similarity	NPD7199	Phase 2
0.7305	Intermediate Similarity	NPD7157	Approved
0.7292	Intermediate Similarity	NPD3019	Approved
0.7292	Intermediate Similarity	NPD3095	Discontinued
0.7273	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5844	Phase 1
0.7248	Intermediate Similarity	NPD2861	Phase 2
0.7246	Intermediate Similarity	NPD3022	Approved
0.7246	Intermediate Similarity	NPD3021	Approved
0.7226	Intermediate Similarity	NPD1358	Approved
0.7219	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2898	Approved
0.7172	Intermediate Similarity	NPD2932	Approved
0.7172	Intermediate Similarity	NPD4059	Approved
0.7162	Intermediate Similarity	NPD1283	Approved
0.716	Intermediate Similarity	NPD1653	Approved
0.7153	Intermediate Similarity	NPD3134	Approved
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6331	Phase 2
0.7135	Intermediate Similarity	NPD7473	Discontinued
0.7133	Intermediate Similarity	NPD9494	Approved
0.7124	Intermediate Similarity	NPD1613	Approved
0.7124	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3496	Discontinued
0.7117	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2438	Suspended
0.7107	Intermediate Similarity	NPD6190	Approved
0.7099	Intermediate Similarity	NPD5699	Approved
0.7095	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7843	Approved
0.7092	Intermediate Similarity	NPD5535	Approved
0.7081	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD27	Approved
0.7076	Intermediate Similarity	NPD2489	Approved
0.7075	Intermediate Similarity	NPD3705	Approved
0.7063	Intermediate Similarity	NPD4198	Discontinued
0.7059	Intermediate Similarity	NPD6232	Discontinued
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7047	Intermediate Similarity	NPD8651	Approved
0.7034	Intermediate Similarity	NPD7741	Discontinued
0.7032	Intermediate Similarity	NPD4097	Suspended
0.7032	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6677	Suspended
0.703	Intermediate Similarity	NPD6873	Phase 2
0.7029	Intermediate Similarity	NPD7240	Approved
0.7025	Intermediate Similarity	NPD7037	Approved
0.7013	Intermediate Similarity	NPD2979	Phase 3
0.7006	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2935	Discontinued
0.6993	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1934	Approved
0.6988	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5585	Approved
0.6977	Remote Similarity	NPD4481	Phase 3
0.6974	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4908	Phase 1
0.6971	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7768	Phase 2
0.6959	Remote Similarity	NPD3051	Approved
0.6959	Remote Similarity	NPD1281	Approved
0.6957	Remote Similarity	NPD7236	Approved
0.6954	Remote Similarity	NPD5647	Approved
0.6949	Remote Similarity	NPD8313	Approved
0.6949	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8312	Approved
0.6946	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1876	Approved
0.6933	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2684	Approved
0.6928	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2970	Approved
0.6919	Remote Similarity	NPD2969	Approved
0.6918	Remote Similarity	NPD4534	Discontinued
0.6918	Remote Similarity	NPD5958	Discontinued
0.6909	Remote Similarity	NPD3455	Phase 2
0.6908	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2161	Phase 2
0.6892	Remote Similarity	NPD3026	Approved
0.6892	Remote Similarity	NPD3023	Approved
0.689	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7906	Approved
0.6887	Remote Similarity	NPD2797	Approved
0.6886	Remote Similarity	NPD5714	Approved
0.6883	Remote Similarity	NPD3764	Approved
0.6883	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6166	Phase 2
0.6875	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3025	Approved
0.6871	Remote Similarity	NPD3024	Approved
0.6864	Remote Similarity	NPD3882	Suspended
0.6862	Remote Similarity	NPD7497	Discontinued
0.6859	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5124	Phase 1
0.6859	Remote Similarity	NPD4340	Discontinued
0.6854	Remote Similarity	NPD7313	Approved
0.6854	Remote Similarity	NPD7310	Approved
0.6854	Remote Similarity	NPD7312	Approved
0.6854	Remote Similarity	NPD7311	Approved
0.6845	Remote Similarity	NPD8455	Phase 2
0.6845	Remote Similarity	NPD1465	Phase 2
0.6845	Remote Similarity	NPD7819	Suspended
0.6842	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6584	Phase 3
0.6839	Remote Similarity	NPD4062	Phase 3
0.6839	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7743	Approved
0.6835	Remote Similarity	NPD2799	Discontinued
0.6835	Remote Similarity	NPD7742	Approved
0.6833	Remote Similarity	NPD8434	Phase 2
0.6832	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7075	Discontinued
0.6824	Remote Similarity	NPD1778	Approved
0.6818	Remote Similarity	NPD7074	Phase 3
0.6816	Remote Similarity	NPD7309	Approved
0.6813	Remote Similarity	NPD2490	Approved
0.6813	Remote Similarity	NPD2488	Approved
0.681	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7041	Phase 2
0.68	Remote Similarity	NPD3818	Discontinued
0.6798	Remote Similarity	NPD7549	Discontinued
0.6792	Remote Similarity	NPD2531	Phase 2
0.679	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5241	Discontinued
0.6786	Remote Similarity	NPD5722	Discontinued
0.6779	Remote Similarity	NPD3847	Discontinued
0.6776	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6362	Approved
0.6774	Remote Similarity	NPD5111	Phase 2
0.6774	Remote Similarity	NPD5109	Approved
0.6774	Remote Similarity	NPD5110	Phase 2
0.6774	Remote Similarity	NPD7985	Registered
0.6774	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3268	Approved
0.6772	Remote Similarity	NPD7680	Approved
0.6772	Remote Similarity	NPD6895	Approved
0.6772	Remote Similarity	NPD6896	Approved
0.677	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3645	Discontinued
0.6768	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5713	Approved
0.6763	Remote Similarity	NPD7315	Approved
0.6761	Remote Similarity	NPD7054	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