NPASS Compound

Structure

CID253807 OpenBabel06191716052D 33 37 0 0 1 0 0 0 0 0999 V2000 -3.6249 -0.9405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1454 0.5927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3466 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8598 -1.1041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3729 -2.9211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -1.9474 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 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 -1.6865 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 -3.4079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 30 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 24 1 0 0 0 0 17 29 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 6 0 0 0 21 26 1 0 0 0 0 21 27 1 0 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 1 0 0 0 24 30 1 1 0 0 0 24 33 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 6 0 0 0 29 7 1 6 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	508.388
LogP:	5.445
LogD:	4.264
LogS:	-3.993
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	4.889
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.817
MDCK Permeability:	1.2089489246136509e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.597
Plasma Protein Binding (PPB):	94.5997085571289%
Volume Distribution (VD):	1.13
Pgp-substrate:	3.868966579437256%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.185
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	10.921
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.484
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.84
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.296
Carcinogencity:	0.299
Eye Corrosion:	0.02
Eye Irritation:	0.032
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC253807

Natural Product ID:	NPC253807
*Common Name:**	(3S,6Ar,6Bs,8S,8As,12As,14Br)-8A-(Hydroxymethyl)-4,4,6A,6B,11,11,14B-Heptamethyl-1,2,3,4A,5,6,7,8,9,10,12,12A,14,14A-Tetradecahydropicene-3,8-Diol
IUPAC Name:	(3S,6aR,6bS,8S,8aS,12aS,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8-diol
Synonyms:
Standard InCHIKey:	YHGVYECWZWIVJC-GEXBJSHGSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-25(2)14-15-30(18-31)20(16-25)19-8-9-22-27(5)12-11-23(32)26(3,4)21(27)10-13-28(22,6)29(19,7)17-24(30)33/h8,20-24,31-33H,9-18H2,1-7H3/t20-,21?,22?,23-,24-,27-,28+,29+,30+/m0/s1
SMILES:	CC1(C)CC[C@@]2(CO)[C@@H](C1)C1=CCC3[C@@]4(C)CC[C@@H](C(C)(C)C4CC[C@@]3(C)[C@]1(C)C[C@@H]2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1706157
PubChem CID:	23641100
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
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
AC50	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		AC50	=	3138.0	nM	PMID[450343]
NPT2	Others	Unspecified		AC50	=	4354.0	nM	PMID[450343]

☑ 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 NPC253807 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	206
0.1-0.2	1753
0.2-0.3	7209
0.3-0.4	16581
0.4-0.5	6968
0.5-0.6	4771
0.6-0.7	3565
0.7-0.8	1237
0.8-0.85	253
0.85-0.9	114
0.9-0.95	11
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC230295
1.0	High Similarity	NPC196753
1.0	High Similarity	NPC98386
1.0	High Similarity	NPC158662
0.9863	High Similarity	NPC53744
0.9861	High Similarity	NPC34177
0.9861	High Similarity	NPC157996
0.9861	High Similarity	NPC40394
0.9861	High Similarity	NPC101475
0.9726	High Similarity	NPC99168
0.9726	High Similarity	NPC474989
0.9726	High Similarity	NPC22955
0.9726	High Similarity	NPC470396
0.9726	High Similarity	NPC300499
0.9722	High Similarity	NPC290598
0.9722	High Similarity	NPC265328
0.9722	High Similarity	NPC30590
0.9722	High Similarity	NPC120098
0.9722	High Similarity	NPC27765
0.9722	High Similarity	NPC122418
0.96	High Similarity	NPC242350
0.9595	High Similarity	NPC291379
0.9583	High Similarity	NPC34700
0.9583	High Similarity	NPC138374
0.9474	High Similarity	NPC47763
0.9467	High Similarity	NPC295131
0.9452	High Similarity	NPC106364
0.9444	High Similarity	NPC100334
0.9351	High Similarity	NPC159168
0.9351	High Similarity	NPC253402
0.9324	High Similarity	NPC472805
0.9324	High Similarity	NPC90979
0.9231	High Similarity	NPC238992
0.9221	High Similarity	NPC304285
0.92	High Similarity	NPC72507
0.9178	High Similarity	NPC91858
0.9103	High Similarity	NPC237795
0.9103	High Similarity	NPC82538
0.9091	High Similarity	NPC116202
0.9041	High Similarity	NPC211009
0.9041	High Similarity	NPC182717
0.9	High Similarity	NPC237344
0.9	High Similarity	NPC213412
0.8919	High Similarity	NPC471797
0.8919	High Similarity	NPC243342
0.8919	High Similarity	NPC477138
0.8904	High Similarity	NPC167706
0.8904	High Similarity	NPC301226
0.8875	High Similarity	NPC133954
0.8875	High Similarity	NPC191965
0.8816	High Similarity	NPC471798
0.8816	High Similarity	NPC477924
0.8816	High Similarity	NPC470758
0.8816	High Similarity	NPC470711
0.88	High Similarity	NPC144075
0.88	High Similarity	NPC291503
0.88	High Similarity	NPC477923
0.88	High Similarity	NPC66566
0.8784	High Similarity	NPC471799
0.8765	High Similarity	NPC95594
0.8765	High Similarity	NPC477579
0.8765	High Similarity	NPC74363
0.8765	High Similarity	NPC475862
0.8765	High Similarity	NPC84121
0.8765	High Similarity	NPC235341
0.8765	High Similarity	NPC137306
0.8734	High Similarity	NPC248886
0.8701	High Similarity	NPC285761
0.8701	High Similarity	NPC244385
0.8701	High Similarity	NPC6978
0.8701	High Similarity	NPC138621
0.8701	High Similarity	NPC167037
0.8684	High Similarity	NPC93662
0.8684	High Similarity	NPC106432
0.8684	High Similarity	NPC470749
0.8684	High Similarity	NPC237460
0.8684	High Similarity	NPC78067
0.8684	High Similarity	NPC189883
0.8684	High Similarity	NPC278091
0.8675	High Similarity	NPC259875
0.8675	High Similarity	NPC293048
0.8675	High Similarity	NPC225585
0.8675	High Similarity	NPC234346
0.8675	High Similarity	NPC59263
0.8675	High Similarity	NPC130520
0.8675	High Similarity	NPC61543
0.8675	High Similarity	NPC121798
0.8675	High Similarity	NPC263393
0.8675	High Similarity	NPC127689
0.8675	High Similarity	NPC187785
0.8675	High Similarity	NPC270768
0.8659	High Similarity	NPC102683
0.8659	High Similarity	NPC130577
0.8659	High Similarity	NPC18064
0.8659	High Similarity	NPC51700
0.8659	High Similarity	NPC88716
0.8659	High Similarity	NPC98442
0.8659	High Similarity	NPC171203
0.8659	High Similarity	NPC142415
0.8659	High Similarity	NPC73064
0.8659	High Similarity	NPC293564
0.8659	High Similarity	NPC68160
0.8659	High Similarity	NPC307426
0.8659	High Similarity	NPC242468
0.8649	High Similarity	NPC110799
0.8649	High Similarity	NPC242001
0.859	High Similarity	NPC273410
0.859	High Similarity	NPC472463
0.859	High Similarity	NPC80530
0.859	High Similarity	NPC1319
0.8571	High Similarity	NPC91594
0.8571	High Similarity	NPC214570
0.8571	High Similarity	NPC130278
0.8571	High Similarity	NPC471432
0.8571	High Similarity	NPC126369
0.8571	High Similarity	NPC86372
0.8571	High Similarity	NPC111110
0.8571	High Similarity	NPC172361
0.8571	High Similarity	NPC130136
0.8571	High Similarity	NPC471433
0.8571	High Similarity	NPC470589
0.8554	High Similarity	NPC52169
0.8554	High Similarity	NPC40552
0.8554	High Similarity	NPC181225
0.8554	High Similarity	NPC470629
0.8554	High Similarity	NPC290690
0.8554	High Similarity	NPC473242
0.8554	High Similarity	NPC182797
0.8554	High Similarity	NPC17733
0.8554	High Similarity	NPC246708
0.8554	High Similarity	NPC474512
0.8553	High Similarity	NPC141071
0.8553	High Similarity	NPC257347
0.8553	High Similarity	NPC212879
0.8553	High Similarity	NPC240235
0.8553	High Similarity	NPC471723
0.8553	High Similarity	NPC231256
0.8553	High Similarity	NPC104387
0.8553	High Similarity	NPC178383
0.8537	High Similarity	NPC72638
0.8519	High Similarity	NPC180834
0.8519	High Similarity	NPC209802
0.8514	High Similarity	NPC92801
0.8514	High Similarity	NPC145498
0.85	High Similarity	NPC30166
0.8493	Intermediate Similarity	NPC94192
0.8493	Intermediate Similarity	NPC208999
0.8481	Intermediate Similarity	NPC102253
0.8481	Intermediate Similarity	NPC13554
0.8481	Intermediate Similarity	NPC322313
0.8481	Intermediate Similarity	NPC236237
0.8481	Intermediate Similarity	NPC236112
0.8471	Intermediate Similarity	NPC228784
0.8471	Intermediate Similarity	NPC155120
0.8471	Intermediate Similarity	NPC324341
0.8471	Intermediate Similarity	NPC966
0.8471	Intermediate Similarity	NPC288833
0.8471	Intermediate Similarity	NPC282616
0.8462	Intermediate Similarity	NPC275910
0.8462	Intermediate Similarity	NPC312328
0.8462	Intermediate Similarity	NPC65897
0.8462	Intermediate Similarity	NPC148977
0.8462	Intermediate Similarity	NPC11908
0.8462	Intermediate Similarity	NPC302041
0.8462	Intermediate Similarity	NPC85346
0.8452	Intermediate Similarity	NPC274330
0.8452	Intermediate Similarity	NPC69627
0.8452	Intermediate Similarity	NPC290972
0.8452	Intermediate Similarity	NPC161751
0.8452	Intermediate Similarity	NPC470588
0.8452	Intermediate Similarity	NPC95246
0.8452	Intermediate Similarity	NPC64872
0.8452	Intermediate Similarity	NPC474972
0.8452	Intermediate Similarity	NPC25906
0.8452	Intermediate Similarity	NPC143232
0.8452	Intermediate Similarity	NPC198664
0.8442	Intermediate Similarity	NPC202642
0.8442	Intermediate Similarity	NPC14112
0.8442	Intermediate Similarity	NPC321016
0.8442	Intermediate Similarity	NPC73875
0.8442	Intermediate Similarity	NPC129165
0.8442	Intermediate Similarity	NPC46160
0.8442	Intermediate Similarity	NPC265588
0.8442	Intermediate Similarity	NPC134330
0.8442	Intermediate Similarity	NPC86305
0.8442	Intermediate Similarity	NPC477925
0.8442	Intermediate Similarity	NPC107059
0.8442	Intermediate Similarity	NPC321381
0.8442	Intermediate Similarity	NPC300324
0.8442	Intermediate Similarity	NPC240604
0.8442	Intermediate Similarity	NPC274079
0.8434	Intermediate Similarity	NPC470620
0.8421	Intermediate Similarity	NPC192638
0.8421	Intermediate Similarity	NPC201048
0.8421	Intermediate Similarity	NPC62657
0.8421	Intermediate Similarity	NPC25511
0.8421	Intermediate Similarity	NPC476366
0.8415	Intermediate Similarity	NPC477578
0.84	Intermediate Similarity	NPC164022
0.8395	Intermediate Similarity	NPC113978

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 NPC253807 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	2041
0.2-0.3	4199
0.3-0.4	1947
0.4-0.5	404
0.5-0.6	174
0.6-0.7	177
0.7-0.8	13
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9863	High Similarity	NPD7645	Phase 2
0.8481	Intermediate Similarity	NPD7525	Registered
0.8312	Intermediate Similarity	NPD6942	Approved
0.8312	Intermediate Similarity	NPD7339	Approved
0.8256	Intermediate Similarity	NPD7515	Phase 2
0.8205	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7748	Approved
0.7674	Intermediate Similarity	NPD3618	Phase 1
0.7647	Intermediate Similarity	NPD4786	Approved
0.7619	Intermediate Similarity	NPD3667	Approved
0.7614	Intermediate Similarity	NPD5328	Approved
0.7609	Intermediate Similarity	NPD7902	Approved
0.7558	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6924	Approved
0.75	Intermediate Similarity	NPD6926	Approved
0.7468	Intermediate Similarity	NPD4243	Approved
0.7444	Intermediate Similarity	NPD6079	Approved
0.7407	Intermediate Similarity	NPD8264	Approved
0.7317	Intermediate Similarity	NPD6933	Approved
0.7284	Intermediate Similarity	NPD4784	Approved
0.7284	Intermediate Similarity	NPD4785	Approved
0.7283	Intermediate Similarity	NPD7900	Approved
0.7283	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6929	Approved
0.725	Intermediate Similarity	NPD7150	Approved
0.725	Intermediate Similarity	NPD7151	Approved
0.725	Intermediate Similarity	NPD7152	Approved
0.7241	Intermediate Similarity	NPD3666	Approved
0.7241	Intermediate Similarity	NPD3665	Phase 1
0.7241	Intermediate Similarity	NPD3133	Approved
0.7215	Intermediate Similarity	NPD6922	Approved
0.7215	Intermediate Similarity	NPD6923	Approved
0.7191	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6930	Phase 2
0.7176	Intermediate Similarity	NPD7509	Discontinued
0.7176	Intermediate Similarity	NPD4748	Discontinued
0.7176	Intermediate Similarity	NPD6931	Approved
0.7174	Intermediate Similarity	NPD4202	Approved
0.7125	Intermediate Similarity	NPD7144	Approved
0.7125	Intermediate Similarity	NPD7143	Approved
0.7053	Intermediate Similarity	NPD4755	Approved
0.7024	Intermediate Similarity	NPD5776	Phase 2
0.7024	Intermediate Similarity	NPD6925	Approved
0.7024	Intermediate Similarity	NPD6932	Approved
0.7	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5275	Approved
0.6988	Remote Similarity	NPD4190	Phase 3
0.6979	Remote Similarity	NPD7638	Approved
0.6947	Remote Similarity	NPD4697	Phase 3
0.6947	Remote Similarity	NPD5221	Approved
0.6947	Remote Similarity	NPD5222	Approved
0.6947	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7145	Approved
0.6932	Remote Similarity	NPD6695	Phase 3
0.6907	Remote Similarity	NPD7640	Approved
0.6907	Remote Similarity	NPD4696	Approved
0.6907	Remote Similarity	NPD5285	Approved
0.6907	Remote Similarity	NPD7639	Approved
0.6907	Remote Similarity	NPD5286	Approved
0.6907	Remote Similarity	NPD4700	Approved
0.6882	Remote Similarity	NPD8035	Phase 2
0.6882	Remote Similarity	NPD8034	Phase 2
0.6875	Remote Similarity	NPD5173	Approved
0.686	Remote Similarity	NPD4195	Approved
0.686	Remote Similarity	NPD6683	Phase 2
0.6854	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3668	Phase 3
0.6848	Remote Similarity	NPD4753	Phase 2
0.6809	Remote Similarity	NPD6399	Phase 3
0.6804	Remote Similarity	NPD5290	Discontinued
0.6782	Remote Similarity	NPD7332	Phase 2
0.6782	Remote Similarity	NPD7514	Phase 3
0.6778	Remote Similarity	NPD6893	Approved
0.6768	Remote Similarity	NPD5211	Phase 2
0.6768	Remote Similarity	NPD5225	Approved
0.6768	Remote Similarity	NPD5226	Approved
0.6768	Remote Similarity	NPD4633	Approved
0.6768	Remote Similarity	NPD5224	Approved
0.6753	Remote Similarity	NPD368	Approved
0.6744	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6402	Approved
0.6733	Remote Similarity	NPD7128	Approved
0.6733	Remote Similarity	NPD6675	Approved
0.6733	Remote Similarity	NPD5739	Approved
0.6705	Remote Similarity	NPD6898	Phase 1
0.6705	Remote Similarity	NPD6902	Approved
0.6703	Remote Similarity	NPD5279	Phase 3
0.67	Remote Similarity	NPD5174	Approved
0.67	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5223	Approved
0.6634	Remote Similarity	NPD5141	Approved
0.663	Remote Similarity	NPD7524	Approved
0.663	Remote Similarity	NPD7750	Discontinued
0.6629	Remote Similarity	NPD4221	Approved
0.6629	Remote Similarity	NPD4223	Phase 3
0.6602	Remote Similarity	NPD7320	Approved
0.6602	Remote Similarity	NPD6899	Approved
0.6602	Remote Similarity	NPD6881	Approved
0.6593	Remote Similarity	NPD5329	Approved
0.6591	Remote Similarity	NPD4695	Discontinued
0.6569	Remote Similarity	NPD4767	Approved
0.6569	Remote Similarity	NPD4768	Approved
0.6556	Remote Similarity	NPD4788	Approved
0.6538	Remote Similarity	NPD6373	Approved
0.6538	Remote Similarity	NPD6372	Approved
0.6535	Remote Similarity	NPD4754	Approved
0.6531	Remote Similarity	NPD6083	Phase 2
0.6531	Remote Similarity	NPD6084	Phase 2
0.6526	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.6522	Remote Similarity	NPD7521	Approved
0.6506	Remote Similarity	NPD4787	Phase 1
0.6505	Remote Similarity	NPD5697	Approved
0.6505	Remote Similarity	NPD5701	Approved
0.6495	Remote Similarity	NPD4629	Approved
0.6495	Remote Similarity	NPD5210	Approved
0.6484	Remote Similarity	NPD4197	Approved
0.6476	Remote Similarity	NPD7102	Approved
0.6476	Remote Similarity	NPD7290	Approved
0.6476	Remote Similarity	NPD6883	Approved
0.6465	Remote Similarity	NPD4225	Approved
0.6452	Remote Similarity	NPD3573	Approved
0.6442	Remote Similarity	NPD5128	Approved
0.6442	Remote Similarity	NPD4729	Approved
0.6442	Remote Similarity	NPD4730	Approved
0.6429	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD8130	Phase 1
0.6415	Remote Similarity	NPD6617	Approved
0.6415	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD6649	Approved
0.6415	Remote Similarity	NPD6869	Approved
0.6415	Remote Similarity	NPD6650	Approved
0.64	Remote Similarity	NPD342	Phase 1
0.6386	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6903	Approved
0.6381	Remote Similarity	NPD6012	Approved
0.6381	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6013	Approved
0.6381	Remote Similarity	NPD6014	Approved
0.6372	Remote Similarity	NPD8328	Phase 3
0.6364	Remote Similarity	NPD3617	Approved
0.6355	Remote Similarity	NPD6882	Approved
0.6355	Remote Similarity	NPD8297	Approved
0.6354	Remote Similarity	NPD7087	Discontinued
0.6346	Remote Similarity	NPD6412	Phase 2
0.6344	Remote Similarity	NPD4519	Discontinued
0.6344	Remote Similarity	NPD4690	Approved
0.6344	Remote Similarity	NPD4623	Approved
0.6344	Remote Similarity	NPD4688	Approved
0.6344	Remote Similarity	NPD4138	Approved
0.6344	Remote Similarity	NPD4693	Phase 3
0.6344	Remote Similarity	NPD4689	Approved
0.6344	Remote Similarity	NPD5205	Approved
0.6337	Remote Similarity	NPD4159	Approved
0.6322	Remote Similarity	NPD6117	Approved
0.6321	Remote Similarity	NPD5250	Approved
0.6321	Remote Similarity	NPD5247	Approved
0.6321	Remote Similarity	NPD5251	Approved
0.6321	Remote Similarity	NPD5248	Approved
0.6321	Remote Similarity	NPD4634	Approved
0.6321	Remote Similarity	NPD5249	Phase 3
0.6316	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6051	Approved
0.6286	Remote Similarity	NPD5168	Approved
0.6286	Remote Similarity	NPD6011	Approved
0.6279	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7632	Discontinued
0.6273	Remote Similarity	NPD7115	Discovery
0.6273	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7614	Phase 1
0.6262	Remote Similarity	NPD5217	Approved
0.6262	Remote Similarity	NPD5216	Approved
0.6262	Remote Similarity	NPD5215	Approved
0.6262	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6116	Phase 1
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD8377	Approved
0.6222	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7328	Approved
0.6216	Remote Similarity	NPD7327	Approved
0.6211	Remote Similarity	NPD4722	Approved
0.6211	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD5737	Approved
0.6211	Remote Similarity	NPD4723	Approved
0.6207	Remote Similarity	NPD3703	Phase 2
0.6195	Remote Similarity	NPD8378	Approved
0.6195	Remote Similarity	NPD8033	Approved
0.6195	Remote Similarity	NPD8296	Approved
0.6195	Remote Similarity	NPD8335	Approved
0.6195	Remote Similarity	NPD8380	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