NPASS Compound

Structure

NPC469327 OpenBabel07101718222D 38 42 0 0 1 0 0 0 0 0999 V2000 -3.1807 0.6880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4772 -2.6216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8719 -1.1076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3603 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8441 1.4668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9152 1.1649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9714 0.1021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -3.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8290 -0.9668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2031 0.9554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5271 -0.0379 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4326 -2.8247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9535 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1745 1.0575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7844 -1.1699 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3835 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5717 0.1652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.4379 -0.4440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3835 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6410 0.5114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -1.9535 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8459 -0.4884 0.0000 C 0 0 2 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 -3.7345 -3.7536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 1.9034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 -3.4186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0862 -2.0988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3669 -0.1422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 8 31 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 30 1 0 0 0 0 13 31 1 0 0 0 0 14 17 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 16 32 1 0 0 0 0 17 1 1 1 0 0 0 17 25 1 0 0 0 0 18 33 2 0 0 0 0 18 37 1 0 0 0 0 19 25 2 0 0 0 0 19 32 1 0 0 0 0 20 26 1 0 0 0 0 20 34 1 1 0 0 0 21 25 1 0 0 0 0 21 35 2 0 0 0 0 22 14 1 6 0 0 0 22 37 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 28 1 0 0 0 0 24 36 2 0 0 0 0 26 30 1 0 0 0 0 26 31 1 0 0 0 0 27 22 1 1 0 0 0 27 29 1 0 0 0 0 27 38 1 0 0 0 0 29 38 1 0 0 0 0 30 7 1 1 0 0 0 31 32 1 1 0 0 0 32 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	236.18
Volume:	257.271
LogP:	3.289
LogD:	2.699
LogS:	-3.356
# Rotatable Bonds:	1
TPSA:	32.76
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.561
Synthetic Accessibility Score:	4.816
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.429
MDCK Permeability:	2.620214581838809e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.784
Plasma Protein Binding (PPB):	57.13343811035156%
Volume Distribution (VD):	1.659
Pgp-substrate:	42.53290557861328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.392
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.449
CYP3A4-inhibitor:	0.163
CYP3A4-substrate:	0.4

ADMET: Excretion

Clearance (CL):	16.346
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.377
Skin Sensitization:	0.303
Carcinogencity:	0.732
Eye Corrosion:	0.081
Eye Irritation:	0.132
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC469327

Natural Product ID:	NPC469327
*Common Name:**	[(1S,3R)-1-[(2R)-3,3-Dimethyloxiran-2-Yl]-3-[(8S,10S,11S,14R)-11-Hydroxy-4,4,8,10,14-Pentamethyl-3,16-Dioxo-2,5,6,7,9,11,12,15-Octahydro-1H-Cyclopenta[A]Phenanthren-17-Yl]Butyl] Acetate
IUPAC Name:	[(1S,3R)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(8S,10S,11S,14R)-11-hydroxy-4,4,8,10,14-pentamethyl-3,16-dioxo-2,5,6,7,9,11,12,15-octahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl] acetate
Synonyms:
Standard InCHIKey:	KOOCQNIPRJEMDH-HAYLINCASA-N
Standard InCHI:	InChI=1S/C32H48O6/c1-17(14-22(37-18(2)33)27-29(5,6)38-27)25-19-15-20(34)26-30(7)12-11-24(36)28(3,4)23(30)10-13-31(26,8)32(19,9)16-21(25)35/h17,20,22-23,26-27,34H,10-16H2,1-9H3/t17-,20+,22+,23?,26?,27-,30+,31+,32+/m1/s1
SMILES:	CC(CC(C1C(O1)(C)C)OC(=O)C)C2=C3CC(C4C5(CCC(=O)C(C5CCC4(C3(CC2=O)C)C)(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL105571
PubChem CID:	44335391
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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	2.9	%	PMID[474603]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	13.3	%	PMID[474603]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	21.1	%	PMID[474603]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	43.8	%	PMID[474603]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	67.3	%	PMID[474603]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	42000.0	nM	PMID[474603]

☑ 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 NPC469327 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	251
0.1-0.2	1614
0.2-0.3	5269
0.3-0.4	10994
0.4-0.5	10430
0.5-0.6	6557
0.6-0.7	5539
0.7-0.8	1969
0.8-0.85	49
0.85-0.9	8
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.957	High Similarity	NPC471777
0.949	High Similarity	NPC9457
0.949	High Similarity	NPC471783
0.9362	High Similarity	NPC471822
0.9255	High Similarity	NPC469329
0.9255	High Similarity	NPC473415
0.9255	High Similarity	NPC180557
0.9255	High Similarity	NPC30677
0.9255	High Similarity	NPC37787
0.9082	High Similarity	NPC469316
0.9043	High Similarity	NPC274046
0.9043	High Similarity	NPC198074
0.9043	High Similarity	NPC469315
0.9	High Similarity	NPC470587
0.8947	High Similarity	NPC240617
0.8936	High Similarity	NPC473166
0.8738	High Similarity	NPC41405
0.8725	High Similarity	NPC473165
0.8654	High Similarity	NPC5284
0.8614	High Similarity	NPC324001
0.8614	High Similarity	NPC264048
0.8515	High Similarity	NPC473163
0.8511	High Similarity	NPC469317
0.8511	High Similarity	NPC469322
0.8511	High Similarity	NPC241875
0.8511	High Similarity	NPC469314
0.8505	High Similarity	NPC284915
0.8491	Intermediate Similarity	NPC152117
0.8491	Intermediate Similarity	NPC234042
0.8469	Intermediate Similarity	NPC473170
0.8454	Intermediate Similarity	NPC477436
0.8454	Intermediate Similarity	NPC477435
0.8411	Intermediate Similarity	NPC255017
0.84	Intermediate Similarity	NPC471582
0.8384	Intermediate Similarity	NPC471039
0.8365	Intermediate Similarity	NPC469318
0.8365	Intermediate Similarity	NPC473173
0.8364	Intermediate Similarity	NPC161065
0.8318	Intermediate Similarity	NPC476163
0.8288	Intermediate Similarity	NPC241192
0.8283	Intermediate Similarity	NPC477438
0.8283	Intermediate Similarity	NPC470016
0.8283	Intermediate Similarity	NPC477437
0.8283	Intermediate Similarity	NPC317586
0.8265	Intermediate Similarity	NPC79117
0.8257	Intermediate Similarity	NPC298278
0.8235	Intermediate Similarity	NPC476897
0.8218	Intermediate Similarity	NPC303777
0.8218	Intermediate Similarity	NPC471784
0.8198	Intermediate Similarity	NPC42673
0.8182	Intermediate Similarity	NPC477439
0.8182	Intermediate Similarity	NPC166906
0.8182	Intermediate Similarity	NPC471040
0.8173	Intermediate Similarity	NPC65523
0.8148	Intermediate Similarity	NPC470063
0.8137	Intermediate Similarity	NPC316964
0.8131	Intermediate Similarity	NPC239097
0.8125	Intermediate Similarity	NPC154491
0.8125	Intermediate Similarity	NPC251226
0.8125	Intermediate Similarity	NPC268530
0.81	Intermediate Similarity	NPC279974
0.8095	Intermediate Similarity	NPC472655
0.8091	Intermediate Similarity	NPC302471
0.8091	Intermediate Similarity	NPC270929
0.8085	Intermediate Similarity	NPC86370
0.8081	Intermediate Similarity	NPC294263
0.8077	Intermediate Similarity	NPC470310
0.8077	Intermediate Similarity	NPC312900
0.8058	Intermediate Similarity	NPC115899
0.8056	Intermediate Similarity	NPC469655
0.8056	Intermediate Similarity	NPC469656
0.8056	Intermediate Similarity	NPC474846
0.8053	Intermediate Similarity	NPC159456
0.8053	Intermediate Similarity	NPC4021
0.8039	Intermediate Similarity	NPC119036
0.8039	Intermediate Similarity	NPC475876
0.8037	Intermediate Similarity	NPC475065
0.8037	Intermediate Similarity	NPC310546
0.8021	Intermediate Similarity	NPC471737
0.802	Intermediate Similarity	NPC327788
0.802	Intermediate Similarity	NPC95565
0.802	Intermediate Similarity	NPC305483
0.802	Intermediate Similarity	NPC328162
0.802	Intermediate Similarity	NPC96859
0.8019	Intermediate Similarity	NPC473284
0.8018	Intermediate Similarity	NPC183580
0.8018	Intermediate Similarity	NPC470493
0.8018	Intermediate Similarity	NPC312824
0.8017	Intermediate Similarity	NPC298841
0.8	Intermediate Similarity	NPC184870
0.8	Intermediate Similarity	NPC471293
0.8	Intermediate Similarity	NPC318332
0.8	Intermediate Similarity	NPC159410
0.8	Intermediate Similarity	NPC135854
0.8	Intermediate Similarity	NPC2436
0.8	Intermediate Similarity	NPC216245
0.8	Intermediate Similarity	NPC74751
0.8	Intermediate Similarity	NPC470251
0.7981	Intermediate Similarity	NPC114540
0.7981	Intermediate Similarity	NPC155332
0.7981	Intermediate Similarity	NPC473928
0.7981	Intermediate Similarity	NPC32577
0.798	Intermediate Similarity	NPC235704
0.798	Intermediate Similarity	NPC473167
0.7963	Intermediate Similarity	NPC470065
0.7961	Intermediate Similarity	NPC266955
0.7961	Intermediate Similarity	NPC88198
0.7961	Intermediate Similarity	NPC471041
0.7961	Intermediate Similarity	NPC117685
0.7959	Intermediate Similarity	NPC77263
0.7959	Intermediate Similarity	NPC229871
0.7959	Intermediate Similarity	NPC469319
0.7959	Intermediate Similarity	NPC250592
0.7946	Intermediate Similarity	NPC329736
0.7944	Intermediate Similarity	NPC94942
0.7944	Intermediate Similarity	NPC475418
0.7944	Intermediate Similarity	NPC473482
0.7944	Intermediate Similarity	NPC469844
0.7944	Intermediate Similarity	NPC318363
0.7941	Intermediate Similarity	NPC224356
0.7941	Intermediate Similarity	NPC132753
0.7941	Intermediate Similarity	NPC175351
0.7941	Intermediate Similarity	NPC26413
0.7941	Intermediate Similarity	NPC151681
0.7941	Intermediate Similarity	NPC121402
0.7941	Intermediate Similarity	NPC473456
0.7941	Intermediate Similarity	NPC292133
0.7928	Intermediate Similarity	NPC243981
0.7925	Intermediate Similarity	NPC231530
0.7925	Intermediate Similarity	NPC181357
0.7925	Intermediate Similarity	NPC265127
0.7925	Intermediate Similarity	NPC278628
0.7925	Intermediate Similarity	NPC102352
0.7921	Intermediate Similarity	NPC200702
0.7921	Intermediate Similarity	NPC470031
0.7921	Intermediate Similarity	NPC139459
0.7921	Intermediate Similarity	NPC139570
0.7921	Intermediate Similarity	NPC255809
0.7917	Intermediate Similarity	NPC197823
0.7905	Intermediate Similarity	NPC471005
0.7905	Intermediate Similarity	NPC180204
0.7905	Intermediate Similarity	NPC33973
0.7905	Intermediate Similarity	NPC70967
0.7905	Intermediate Similarity	NPC112009
0.79	Intermediate Similarity	NPC170220
0.79	Intermediate Similarity	NPC214756
0.79	Intermediate Similarity	NPC86368
0.79	Intermediate Similarity	NPC272075
0.79	Intermediate Similarity	NPC474185
0.79	Intermediate Similarity	NPC107674
0.79	Intermediate Similarity	NPC141497
0.79	Intermediate Similarity	NPC295643
0.789	Intermediate Similarity	NPC43775
0.789	Intermediate Similarity	NPC474229
0.7885	Intermediate Similarity	NPC233012
0.7885	Intermediate Similarity	NPC54909
0.7879	Intermediate Similarity	NPC20388
0.7879	Intermediate Similarity	NPC471896
0.7876	Intermediate Similarity	NPC61520
0.7876	Intermediate Similarity	NPC230513
0.787	Intermediate Similarity	NPC218853
0.7864	Intermediate Similarity	NPC58942
0.7864	Intermediate Similarity	NPC471966
0.7864	Intermediate Similarity	NPC470068
0.7864	Intermediate Similarity	NPC260149
0.7864	Intermediate Similarity	NPC470067
0.7864	Intermediate Similarity	NPC470066
0.7864	Intermediate Similarity	NPC114274
0.7857	Intermediate Similarity	NPC80335
0.7857	Intermediate Similarity	NPC167606
0.7857	Intermediate Similarity	NPC474677
0.7857	Intermediate Similarity	NPC55296
0.7857	Intermediate Similarity	NPC286528
0.7857	Intermediate Similarity	NPC140055
0.7857	Intermediate Similarity	NPC470492
0.7857	Intermediate Similarity	NPC471854
0.7857	Intermediate Similarity	NPC20302
0.7857	Intermediate Similarity	NPC477252
0.785	Intermediate Similarity	NPC144854
0.785	Intermediate Similarity	NPC475294
0.785	Intermediate Similarity	NPC220974
0.785	Intermediate Similarity	NPC3316
0.785	Intermediate Similarity	NPC44063
0.785	Intermediate Similarity	NPC330011
0.785	Intermediate Similarity	NPC329048
0.7845	Intermediate Similarity	NPC469790
0.7843	Intermediate Similarity	NPC154526
0.7843	Intermediate Similarity	NPC7124
0.7843	Intermediate Similarity	NPC13949
0.7843	Intermediate Similarity	NPC472362
0.7843	Intermediate Similarity	NPC98874
0.7843	Intermediate Similarity	NPC120708
0.7843	Intermediate Similarity	NPC472363
0.7843	Intermediate Similarity	NPC471153
0.7843	Intermediate Similarity	NPC328371
0.7843	Intermediate Similarity	NPC230151
0.7843	Intermediate Similarity	NPC104568
0.7843	Intermediate Similarity	NPC327179
0.7843	Intermediate Similarity	NPC471775
0.7838	Intermediate Similarity	NPC473798

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 NPC469327 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1986
0.2-0.3	3857
0.3-0.4	2020
0.4-0.5	619
0.5-0.6	209
0.6-0.7	177
0.7-0.8	60
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8148	Intermediate Similarity	NPD8297	Approved
0.8095	Intermediate Similarity	NPD6675	Approved
0.8095	Intermediate Similarity	NPD6402	Approved
0.8095	Intermediate Similarity	NPD5739	Approved
0.8095	Intermediate Similarity	NPD7128	Approved
0.8	Intermediate Similarity	NPD7748	Approved
0.7944	Intermediate Similarity	NPD6881	Approved
0.7944	Intermediate Similarity	NPD6899	Approved
0.7944	Intermediate Similarity	NPD7320	Approved
0.789	Intermediate Similarity	NPD8130	Phase 1
0.787	Intermediate Similarity	NPD6373	Approved
0.787	Intermediate Similarity	NPD6372	Approved
0.7857	Intermediate Similarity	NPD7115	Discovery
0.785	Intermediate Similarity	NPD5701	Approved
0.785	Intermediate Similarity	NPD5697	Approved
0.78	Intermediate Similarity	NPD7515	Phase 2
0.7798	Intermediate Similarity	NPD7290	Approved
0.7798	Intermediate Similarity	NPD6883	Approved
0.7798	Intermediate Similarity	NPD7102	Approved
0.7778	Intermediate Similarity	NPD5328	Approved
0.7767	Intermediate Similarity	NPD7902	Approved
0.7727	Intermediate Similarity	NPD6869	Approved
0.7727	Intermediate Similarity	NPD6649	Approved
0.7727	Intermediate Similarity	NPD6847	Approved
0.7727	Intermediate Similarity	NPD6617	Approved
0.7727	Intermediate Similarity	NPD6650	Approved
0.7706	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6012	Approved
0.7706	Intermediate Similarity	NPD6013	Approved
0.7706	Intermediate Similarity	NPD6014	Approved
0.7658	Intermediate Similarity	NPD6882	Approved
0.7624	Intermediate Similarity	NPD6079	Approved
0.7615	Intermediate Similarity	NPD6011	Approved
0.7596	Intermediate Similarity	NPD6083	Phase 2
0.7596	Intermediate Similarity	NPD4755	Approved
0.7596	Intermediate Similarity	NPD6084	Phase 2
0.7593	Intermediate Similarity	NPD6008	Approved
0.7568	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6399	Phase 3
0.7524	Intermediate Similarity	NPD7638	Approved
0.7477	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7900	Approved
0.7475	Intermediate Similarity	NPD3618	Phase 1
0.7453	Intermediate Similarity	NPD5285	Approved
0.7453	Intermediate Similarity	NPD7639	Approved
0.7453	Intermediate Similarity	NPD5286	Approved
0.7453	Intermediate Similarity	NPD4700	Approved
0.7453	Intermediate Similarity	NPD4696	Approved
0.7453	Intermediate Similarity	NPD7640	Approved
0.7451	Intermediate Similarity	NPD8035	Phase 2
0.7451	Intermediate Similarity	NPD8034	Phase 2
0.7434	Intermediate Similarity	NPD4632	Approved
0.7374	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7736	Approved
0.735	Intermediate Similarity	NPD6319	Approved
0.7333	Intermediate Similarity	NPD5221	Approved
0.7333	Intermediate Similarity	NPD4697	Phase 3
0.7333	Intermediate Similarity	NPD5222	Approved
0.7333	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7632	Discontinued
0.7315	Intermediate Similarity	NPD5226	Approved
0.7315	Intermediate Similarity	NPD5225	Approved
0.7315	Intermediate Similarity	NPD4633	Approved
0.7315	Intermediate Similarity	NPD5224	Approved
0.7315	Intermediate Similarity	NPD5211	Phase 2
0.7311	Intermediate Similarity	NPD7604	Phase 2
0.7304	Intermediate Similarity	NPD6274	Approved
0.73	Intermediate Similarity	NPD6684	Approved
0.73	Intermediate Similarity	NPD7334	Approved
0.73	Intermediate Similarity	NPD7146	Approved
0.73	Intermediate Similarity	NPD7521	Approved
0.73	Intermediate Similarity	NPD6409	Approved
0.73	Intermediate Similarity	NPD5330	Approved
0.7273	Intermediate Similarity	NPD8293	Discontinued
0.7273	Intermediate Similarity	NPD4786	Approved
0.7265	Intermediate Similarity	NPD7101	Approved
0.7265	Intermediate Similarity	NPD7100	Approved
0.7264	Intermediate Similarity	NPD5173	Approved
0.725	Intermediate Similarity	NPD7492	Approved
0.7248	Intermediate Similarity	NPD5175	Approved
0.7248	Intermediate Similarity	NPD5174	Approved
0.7245	Intermediate Similarity	NPD3667	Approved
0.7241	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6009	Approved
0.7238	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5695	Phase 3
0.7232	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3573	Approved
0.7222	Intermediate Similarity	NPD5223	Approved
0.7212	Intermediate Similarity	NPD4202	Approved
0.7207	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6059	Approved
0.7203	Intermediate Similarity	NPD6054	Approved
0.7196	Intermediate Similarity	NPD4225	Approved
0.7196	Intermediate Similarity	NPD5696	Approved
0.719	Intermediate Similarity	NPD6616	Approved
0.719	Intermediate Similarity	NPD7507	Approved
0.7182	Intermediate Similarity	NPD5141	Approved
0.7179	Intermediate Similarity	NPD6335	Approved
0.7167	Intermediate Similarity	NPD8328	Phase 3
0.7158	Intermediate Similarity	NPD6117	Approved
0.7157	Intermediate Similarity	NPD6903	Approved
0.7157	Intermediate Similarity	NPD5737	Approved
0.7157	Intermediate Similarity	NPD6672	Approved
0.7155	Intermediate Similarity	NPD6868	Approved
0.7143	Intermediate Similarity	NPD6909	Approved
0.7143	Intermediate Similarity	NPD6908	Approved
0.7143	Intermediate Similarity	NPD5983	Phase 2
0.7131	Intermediate Similarity	NPD7078	Approved
0.7117	Intermediate Similarity	NPD4768	Approved
0.7117	Intermediate Similarity	NPD4767	Approved
0.7115	Intermediate Similarity	NPD6411	Approved
0.71	Intermediate Similarity	NPD3665	Phase 1
0.71	Intermediate Similarity	NPD3133	Approved
0.71	Intermediate Similarity	NPD3666	Approved
0.7094	Intermediate Similarity	NPD6317	Approved
0.7091	Intermediate Similarity	NPD4754	Approved
0.7087	Intermediate Similarity	NPD4753	Phase 2
0.7083	Intermediate Similarity	NPD6116	Phase 1
0.7083	Intermediate Similarity	NPD6370	Approved
0.7054	Intermediate Similarity	NPD6412	Phase 2
0.7049	Intermediate Similarity	NPD6336	Discontinued
0.7034	Intermediate Similarity	NPD6313	Approved
0.7034	Intermediate Similarity	NPD6314	Approved
0.7018	Intermediate Similarity	NPD4634	Approved
0.7016	Intermediate Similarity	NPD7319	Approved
0.701	Intermediate Similarity	NPD6697	Approved
0.701	Intermediate Similarity	NPD6115	Approved
0.701	Intermediate Similarity	NPD6118	Approved
0.701	Intermediate Similarity	NPD6114	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.7	Intermediate Similarity	NPD6015	Approved
0.6991	Remote Similarity	NPD4730	Approved
0.6991	Remote Similarity	NPD4729	Approved
0.6991	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5128	Approved
0.6961	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5988	Approved
0.6923	Remote Similarity	NPD6904	Approved
0.6923	Remote Similarity	NPD6101	Approved
0.6923	Remote Similarity	NPD6673	Approved
0.6923	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6080	Approved
0.6875	Remote Similarity	NPD3703	Phase 2
0.687	Remote Similarity	NPD5250	Approved
0.687	Remote Similarity	NPD5251	Approved
0.687	Remote Similarity	NPD5248	Approved
0.687	Remote Similarity	NPD5249	Phase 3
0.687	Remote Similarity	NPD5247	Approved
0.6869	Remote Similarity	NPD7525	Registered
0.686	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6686	Approved
0.6837	Remote Similarity	NPD3617	Approved
0.6832	Remote Similarity	NPD4788	Approved
0.6822	Remote Similarity	NPD6001	Approved
0.681	Remote Similarity	NPD5217	Approved
0.681	Remote Similarity	NPD5215	Approved
0.681	Remote Similarity	NPD5216	Approved
0.6765	Remote Similarity	NPD3668	Phase 3
0.6759	Remote Similarity	NPD5210	Approved
0.6759	Remote Similarity	NPD4629	Approved
0.6737	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4221	Approved
0.6733	Remote Similarity	NPD4223	Phase 3
0.6724	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5135	Approved
0.6724	Remote Similarity	NPD5169	Approved
0.6721	Remote Similarity	NPD8033	Approved
0.6702	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5329	Approved
0.6696	Remote Similarity	NPD5168	Approved
0.6695	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6639	Remote Similarity	NPD8377	Approved
0.6639	Remote Similarity	NPD8294	Approved
0.6636	Remote Similarity	NPD5693	Phase 1
0.6636	Remote Similarity	NPD5284	Approved
0.6636	Remote Similarity	NPD5281	Approved
0.6636	Remote Similarity	NPD6050	Approved
0.6635	Remote Similarity	NPD6098	Approved
0.6635	Remote Similarity	NPD5279	Phase 3
0.6612	Remote Similarity	NPD7328	Approved
0.6612	Remote Similarity	NPD7327	Approved
0.661	Remote Similarity	NPD6053	Discontinued
0.6606	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4197	Approved
0.66	Remote Similarity	NPD7645	Phase 2
0.6585	Remote Similarity	NPD8379	Approved
0.6585	Remote Similarity	NPD8335	Approved
0.6585	Remote Similarity	NPD8378	Approved
0.6585	Remote Similarity	NPD8296	Approved
0.6585	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