NPASS Compound

Structure

NPC473415 OpenBabel07101718222D 38 41 0 0 1 0 0 0 0 0999 V2000 3.0303 -2.8973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2357 -6.5246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0243 2.3097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0481 2.3097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8125 -5.1724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0871 -5.8256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4484 0.4037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3476 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7738 -0.1864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4223 -3.4198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0755 -2.6944 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7192 -6.7275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7738 -1.7659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7239 -4.3482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6908 0.9762 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3816 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0707 -5.0737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5362 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1159 -4.8707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 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 1.0209 -7.6559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6788 -4.5512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1858 -3.9423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3724 -6.0021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 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 14 1 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 30 1 0 0 0 0 14 31 1 0 0 0 0 15 32 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 1 1 6 0 0 0 18 20 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 21 2 0 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 34 1 6 0 0 0 23 27 1 0 0 0 0 23 35 1 6 0 0 0 24 28 1 0 0 0 0 24 30 1 0 0 0 0 25 28 1 0 0 0 0 25 36 2 0 0 0 0 26 30 1 0 0 0 0 26 32 1 0 0 0 0 27 29 1 0 0 0 0 27 38 1 1 0 0 0 29 37 1 0 0 0 0 30 7 1 6 0 0 0 31 32 1 1 0 0 0 32 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.38
Volume:	572.634
LogP:	3.972
LogD:	3.296
LogS:	-4.285
# Rotatable Bonds:	7
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.314
Synthetic Accessibility Score:	5.193
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
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:	-5.215
MDCK Permeability:	1.80344759428408e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.295
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.784
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.717
Plasma Protein Binding (PPB):	89.21283721923828%
Volume Distribution (VD):	0.95
Pgp-substrate:	4.706972599029541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.248
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.289
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.796
CYP3A4-substrate:	0.753

ADMET: Excretion

Clearance (CL):	4.778
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.26
Drug-inuced Liver Injury (DILI):	0.123
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.822
Skin Sensitization:	0.035
Carcinogencity:	0.232
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC473415

Natural Product ID:	NPC473415
*Common Name:**	[(3R,4S,6R)-2,4-Dihydroxy-6-[(8S,10S,11S,14R)-11-Hydroxy-4,4,8,10,14-Pentamethyl-3-Oxo-1,2,5,6,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-17-Yl]-2-Methylheptan-3-Yl] Acetate
IUPAC Name:	[(3R,4S,6R)-2,4-dihydroxy-6-[(8S,10S,11S,14R)-11-hydroxy-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-yl] acetate
Synonyms:
Standard InCHIKey:	WXHUQVMHWUQNTG-CPQDFQMASA-N
Standard InCHI:	InChI=1S/C32H52O6/c1-18(16-23(35)27(29(5,6)37)38-19(2)33)20-10-14-31(8)21(20)17-22(34)26-30(7)13-12-25(36)28(3,4)24(30)11-15-32(26,31)9/h18,22-24,26-27,34-35,37H,10-17H2,1-9H3/t18-,22+,23+,24?,26?,27-,30+,31+,32+/m1/s1
SMILES:	CC(CC(C(C(C)(C)O)OC(=O)C)O)C1=C2CC(C3C4(CCC(=O)C(C4CCC3(C2(CC1)C)C)(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL421397
PubChem CID:	10075759
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[544607]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	6.4	%	PMID[544607]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	13.4	%	PMID[544607]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	71.0	%	PMID[544607]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	111.5	%	PMID[544607]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	10000.0	nM	PMID[544607]

☑ 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 NPC473415 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	228
0.1-0.2	1428
0.2-0.3	4767
0.3-0.4	12215
0.4-0.5	9765
0.5-0.6	5950
0.6-0.7	5590
0.7-0.8	2562
0.8-0.85	148
0.85-0.9	25
0.9-0.95	13
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC37787
1.0	High Similarity	NPC469329
1.0	High Similarity	NPC30677
1.0	High Similarity	NPC180557
0.9667	High Similarity	NPC471777
0.9659	High Similarity	NPC473166
0.9362	High Similarity	NPC469316
0.9333	High Similarity	NPC198074
0.9333	High Similarity	NPC274046
0.9263	High Similarity	NPC324001
0.9255	High Similarity	NPC469327
0.9231	High Similarity	NPC240617
0.9205	High Similarity	NPC241875
0.9205	High Similarity	NPC469317
0.9205	High Similarity	NPC469314
0.9032	High Similarity	NPC471822
0.898	High Similarity	NPC469318
0.898	High Similarity	NPC473173
0.898	High Similarity	NPC471783
0.898	High Similarity	NPC9457
0.8878	High Similarity	NPC470587
0.8842	High Similarity	NPC471784
0.8842	High Similarity	NPC303777
0.8778	High Similarity	NPC469322
0.875	High Similarity	NPC86370
0.871	High Similarity	NPC469315
0.8687	High Similarity	NPC472655
0.8614	High Similarity	NPC41405
0.8602	High Similarity	NPC473167
0.8587	High Similarity	NPC469319
0.8587	High Similarity	NPC229871
0.8529	High Similarity	NPC5284
0.8526	High Similarity	NPC279974
0.8485	Intermediate Similarity	NPC264048
0.8469	Intermediate Similarity	NPC54909
0.8469	Intermediate Similarity	NPC476897
0.8469	Intermediate Similarity	NPC233012
0.8454	Intermediate Similarity	NPC470066
0.8454	Intermediate Similarity	NPC119036
0.8454	Intermediate Similarity	NPC470068
0.8454	Intermediate Similarity	NPC470067
0.8438	Intermediate Similarity	NPC230151
0.8431	Intermediate Similarity	NPC218853
0.8421	Intermediate Similarity	NPC159410
0.8404	Intermediate Similarity	NPC235704
0.8384	Intermediate Similarity	NPC473163
0.8367	Intermediate Similarity	NPC473176
0.8367	Intermediate Similarity	NPC167974
0.8365	Intermediate Similarity	NPC470063
0.8365	Intermediate Similarity	NPC234042
0.8365	Intermediate Similarity	NPC152117
0.835	Intermediate Similarity	NPC250956
0.8333	Intermediate Similarity	NPC473170
0.8317	Intermediate Similarity	NPC475414
0.8317	Intermediate Similarity	NPC173172
0.8316	Intermediate Similarity	NPC107674
0.8316	Intermediate Similarity	NPC86368
0.8316	Intermediate Similarity	NPC141497
0.8316	Intermediate Similarity	NPC170220
0.8298	Intermediate Similarity	NPC471896
0.8298	Intermediate Similarity	NPC473269
0.8286	Intermediate Similarity	NPC255017
0.8283	Intermediate Similarity	NPC470054
0.8261	Intermediate Similarity	NPC73038
0.8261	Intermediate Similarity	NPC56588
0.8261	Intermediate Similarity	NPC325594
0.8252	Intermediate Similarity	NPC5475
0.8252	Intermediate Similarity	NPC173905
0.8252	Intermediate Similarity	NPC475065
0.8252	Intermediate Similarity	NPC284828
0.8252	Intermediate Similarity	NPC472216
0.8247	Intermediate Similarity	NPC120708
0.8247	Intermediate Similarity	NPC327179
0.8247	Intermediate Similarity	NPC327788
0.8235	Intermediate Similarity	NPC475176
0.8235	Intermediate Similarity	NPC473165
0.8235	Intermediate Similarity	NPC473284
0.8235	Intermediate Similarity	NPC255387
0.8235	Intermediate Similarity	NPC131665
0.8229	Intermediate Similarity	NPC296164
0.8218	Intermediate Similarity	NPC471293
0.8211	Intermediate Similarity	NPC26888
0.8211	Intermediate Similarity	NPC189520
0.8211	Intermediate Similarity	NPC212301
0.8211	Intermediate Similarity	NPC470590
0.8211	Intermediate Similarity	NPC86266
0.8211	Intermediate Similarity	NPC77099
0.8211	Intermediate Similarity	NPC110657
0.8211	Intermediate Similarity	NPC60755
0.8211	Intermediate Similarity	NPC285184
0.82	Intermediate Similarity	NPC296879
0.82	Intermediate Similarity	NPC473928
0.82	Intermediate Similarity	NPC470053
0.82	Intermediate Similarity	NPC477054
0.82	Intermediate Similarity	NPC471119
0.8191	Intermediate Similarity	NPC474704
0.8191	Intermediate Similarity	NPC250592
0.8191	Intermediate Similarity	NPC32830
0.8191	Intermediate Similarity	NPC475921
0.8191	Intermediate Similarity	NPC77263
0.8191	Intermediate Similarity	NPC474889
0.8191	Intermediate Similarity	NPC30522
0.8173	Intermediate Similarity	NPC470065
0.8172	Intermediate Similarity	NPC138756
0.8163	Intermediate Similarity	NPC259788
0.8163	Intermediate Similarity	NPC255589
0.8163	Intermediate Similarity	NPC247139
0.8163	Intermediate Similarity	NPC9613
0.8155	Intermediate Similarity	NPC472217
0.8155	Intermediate Similarity	NPC472219
0.8155	Intermediate Similarity	NPC258323
0.8155	Intermediate Similarity	NPC475418
0.8155	Intermediate Similarity	NPC318363
0.8155	Intermediate Similarity	NPC472218
0.8155	Intermediate Similarity	NPC473482
0.8144	Intermediate Similarity	NPC195715
0.8144	Intermediate Similarity	NPC32118
0.8144	Intermediate Similarity	NPC473648
0.8137	Intermediate Similarity	NPC477877
0.8137	Intermediate Similarity	NPC475494
0.8125	Intermediate Similarity	NPC473690
0.8125	Intermediate Similarity	NPC287118
0.8125	Intermediate Similarity	NPC136313
0.8125	Intermediate Similarity	NPC471902
0.8125	Intermediate Similarity	NPC275809
0.8125	Intermediate Similarity	NPC477435
0.8125	Intermediate Similarity	NPC307335
0.8125	Intermediate Similarity	NPC133579
0.8125	Intermediate Similarity	NPC477436
0.8125	Intermediate Similarity	NPC474806
0.8125	Intermediate Similarity	NPC74855
0.8119	Intermediate Similarity	NPC471005
0.8119	Intermediate Similarity	NPC222153
0.8119	Intermediate Similarity	NPC218513
0.8119	Intermediate Similarity	NPC55954
0.8105	Intermediate Similarity	NPC175628
0.8105	Intermediate Similarity	NPC111110
0.8105	Intermediate Similarity	NPC111585
0.8105	Intermediate Similarity	NPC472307
0.8105	Intermediate Similarity	NPC474728
0.8105	Intermediate Similarity	NPC120840
0.8105	Intermediate Similarity	NPC113989
0.8105	Intermediate Similarity	NPC49320
0.8105	Intermediate Similarity	NPC126369
0.8105	Intermediate Similarity	NPC148414
0.8105	Intermediate Similarity	NPC470589
0.81	Intermediate Similarity	NPC477052
0.81	Intermediate Similarity	NPC477051
0.81	Intermediate Similarity	NPC289670
0.81	Intermediate Similarity	NPC115899
0.81	Intermediate Similarity	NPC477053
0.8085	Intermediate Similarity	NPC242864
0.8085	Intermediate Similarity	NPC255176
0.8085	Intermediate Similarity	NPC4309
0.8077	Intermediate Similarity	NPC477070
0.8077	Intermediate Similarity	NPC477069
0.8065	Intermediate Similarity	NPC324063
0.8065	Intermediate Similarity	NPC471737
0.8061	Intermediate Similarity	NPC73004
0.8061	Intermediate Similarity	NPC204961
0.8061	Intermediate Similarity	NPC158371
0.8061	Intermediate Similarity	NPC88847
0.8061	Intermediate Similarity	NPC173744
0.8061	Intermediate Similarity	NPC259733
0.8061	Intermediate Similarity	NPC207922
0.8061	Intermediate Similarity	NPC471039
0.8058	Intermediate Similarity	NPC329048
0.8058	Intermediate Similarity	NPC330011
0.8043	Intermediate Similarity	NPC473157
0.8043	Intermediate Similarity	NPC171789
0.8041	Intermediate Similarity	NPC231063
0.8041	Intermediate Similarity	NPC191412
0.8041	Intermediate Similarity	NPC263548
0.8041	Intermediate Similarity	NPC88116
0.8041	Intermediate Similarity	NPC49670
0.8041	Intermediate Similarity	NPC114159
0.8041	Intermediate Similarity	NPC78580
0.8041	Intermediate Similarity	NPC145667
0.8041	Intermediate Similarity	NPC74751
0.8041	Intermediate Similarity	NPC282395
0.8041	Intermediate Similarity	NPC174051
0.8041	Intermediate Similarity	NPC6818
0.8041	Intermediate Similarity	NPC23621
0.8041	Intermediate Similarity	NPC184006
0.8041	Intermediate Similarity	NPC20235
0.8041	Intermediate Similarity	NPC67831
0.8041	Intermediate Similarity	NPC299996
0.8041	Intermediate Similarity	NPC32407
0.8039	Intermediate Similarity	NPC473175
0.8039	Intermediate Similarity	NPC470060
0.8039	Intermediate Similarity	NPC65523
0.8039	Intermediate Similarity	NPC470064
0.8039	Intermediate Similarity	NPC470061
0.8039	Intermediate Similarity	NPC470062
0.8039	Intermediate Similarity	NPC470043
0.8039	Intermediate Similarity	NPC470059
0.8039	Intermediate Similarity	NPC470057
0.8039	Intermediate Similarity	NPC470058
0.8037	Intermediate Similarity	NPC284915
0.8021	Intermediate Similarity	NPC71074

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 NPC473415 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1836
0.2-0.3	3790
0.3-0.4	2181
0.4-0.5	643
0.5-0.6	238
0.6-0.7	195
0.7-0.8	64
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8041	Intermediate Similarity	NPD7748	Approved
0.7938	Intermediate Similarity	NPD6399	Phase 3
0.785	Intermediate Similarity	NPD8297	Approved
0.7835	Intermediate Similarity	NPD8035	Phase 2
0.7835	Intermediate Similarity	NPD7515	Phase 2
0.7835	Intermediate Similarity	NPD8034	Phase 2
0.78	Intermediate Similarity	NPD7902	Approved
0.7788	Intermediate Similarity	NPD7128	Approved
0.7788	Intermediate Similarity	NPD5739	Approved
0.7788	Intermediate Similarity	NPD6675	Approved
0.7788	Intermediate Similarity	NPD6402	Approved
0.7766	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7115	Discovery
0.766	Intermediate Similarity	NPD4786	Approved
0.7642	Intermediate Similarity	NPD7320	Approved
0.7642	Intermediate Similarity	NPD6881	Approved
0.7642	Intermediate Similarity	NPD6899	Approved
0.7634	Intermediate Similarity	NPD3667	Approved
0.7624	Intermediate Similarity	NPD6084	Phase 2
0.7624	Intermediate Similarity	NPD6083	Phase 2
0.7593	Intermediate Similarity	NPD8130	Phase 1
0.757	Intermediate Similarity	NPD6372	Approved
0.757	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD6373	Approved
0.7556	Intermediate Similarity	NPD6117	Approved
0.7549	Intermediate Similarity	NPD7638	Approved
0.7547	Intermediate Similarity	NPD5701	Approved
0.7547	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.7476	Intermediate Similarity	NPD7640	Approved
0.7476	Intermediate Similarity	NPD7639	Approved
0.7473	Intermediate Similarity	NPD6116	Phase 1
0.7449	Intermediate Similarity	NPD5328	Approved
0.7431	Intermediate Similarity	NPD6617	Approved
0.7431	Intermediate Similarity	NPD6869	Approved
0.7431	Intermediate Similarity	NPD6847	Approved
0.7431	Intermediate Similarity	NPD6649	Approved
0.7431	Intermediate Similarity	NPD6650	Approved
0.7411	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6012	Approved
0.7407	Intermediate Similarity	NPD6013	Approved
0.7407	Intermediate Similarity	NPD6014	Approved
0.7391	Intermediate Similarity	NPD6118	Approved
0.7391	Intermediate Similarity	NPD6115	Approved
0.7391	Intermediate Similarity	NPD6114	Approved
0.7391	Intermediate Similarity	NPD6697	Approved
0.7379	Intermediate Similarity	NPD4225	Approved
0.7364	Intermediate Similarity	NPD6882	Approved
0.7347	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.7333	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6409	Approved
0.732	Intermediate Similarity	NPD6684	Approved
0.732	Intermediate Similarity	NPD7521	Approved
0.732	Intermediate Similarity	NPD5330	Approved
0.732	Intermediate Similarity	NPD7334	Approved
0.732	Intermediate Similarity	NPD7146	Approved
0.7315	Intermediate Similarity	NPD6011	Approved
0.73	Intermediate Similarity	NPD6079	Approved
0.7297	Intermediate Similarity	NPD4632	Approved
0.7282	Intermediate Similarity	NPD4755	Approved
0.7273	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5695	Phase 3
0.7234	Intermediate Similarity	NPD7525	Registered
0.7228	Intermediate Similarity	NPD4202	Approved
0.7222	Intermediate Similarity	NPD6412	Phase 2
0.7217	Intermediate Similarity	NPD6319	Approved
0.7212	Intermediate Similarity	NPD5696	Approved
0.7182	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6672	Approved
0.7172	Intermediate Similarity	NPD6903	Approved
0.7172	Intermediate Similarity	NPD5737	Approved
0.7156	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5285	Approved
0.7143	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD5286	Approved
0.7143	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD8133	Approved
0.7129	Intermediate Similarity	NPD6411	Approved
0.7113	Intermediate Similarity	NPD3668	Phase 3
0.7113	Intermediate Similarity	NPD3133	Approved
0.7113	Intermediate Similarity	NPD3665	Phase 1
0.7113	Intermediate Similarity	NPD3666	Approved
0.7111	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4753	Phase 2
0.7087	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7736	Approved
0.7079	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7507	Approved
0.7034	Intermediate Similarity	NPD8328	Phase 3
0.7019	Intermediate Similarity	NPD4697	Phase 3
0.7019	Intermediate Similarity	NPD5222	Approved
0.7019	Intermediate Similarity	NPD5221	Approved
0.7019	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6274	Approved
0.701	Intermediate Similarity	NPD4788	Approved
0.7009	Intermediate Similarity	NPD4633	Approved
0.7009	Intermediate Similarity	NPD5226	Approved
0.7009	Intermediate Similarity	NPD5225	Approved
0.7009	Intermediate Similarity	NPD5224	Approved
0.7009	Intermediate Similarity	NPD5211	Phase 2
0.7	Intermediate Similarity	NPD8293	Discontinued
0.7	Intermediate Similarity	NPD6686	Approved
0.6983	Remote Similarity	NPD7101	Approved
0.6983	Remote Similarity	NPD7100	Approved
0.6975	Remote Similarity	NPD7492	Approved
0.6972	Remote Similarity	NPD6008	Approved
0.697	Remote Similarity	NPD6098	Approved
0.697	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6009	Approved
0.6952	Remote Similarity	NPD5173	Approved
0.6947	Remote Similarity	NPD7645	Phase 2
0.6944	Remote Similarity	NPD5174	Approved
0.6944	Remote Similarity	NPD5175	Approved
0.6931	Remote Similarity	NPD6673	Approved
0.6931	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6080	Approved
0.6931	Remote Similarity	NPD6101	Approved
0.6931	Remote Similarity	NPD6904	Approved
0.6923	Remote Similarity	NPD5777	Approved
0.6923	Remote Similarity	NPD6054	Approved
0.6923	Remote Similarity	NPD6059	Approved
0.6917	Remote Similarity	NPD6616	Approved
0.6916	Remote Similarity	NPD5223	Approved
0.6909	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3573	Approved
0.6897	Remote Similarity	NPD6335	Approved
0.6891	Remote Similarity	NPD7604	Phase 2
0.6889	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7319	Approved
0.6882	Remote Similarity	NPD3703	Phase 2
0.6881	Remote Similarity	NPD5141	Approved
0.6875	Remote Similarity	NPD4634	Approved
0.687	Remote Similarity	NPD6868	Approved
0.6864	Remote Similarity	NPD8033	Approved
0.6864	Remote Similarity	NPD6909	Approved
0.6864	Remote Similarity	NPD5983	Phase 2
0.6864	Remote Similarity	NPD6908	Approved
0.686	Remote Similarity	NPD7078	Approved
0.6842	Remote Similarity	NPD3617	Approved
0.6818	Remote Similarity	NPD4767	Approved
0.6818	Remote Similarity	NPD4768	Approved
0.6813	Remote Similarity	NPD4244	Approved
0.6813	Remote Similarity	NPD4245	Approved
0.681	Remote Similarity	NPD6317	Approved
0.6807	Remote Similarity	NPD6370	Approved
0.6789	Remote Similarity	NPD4754	Approved
0.678	Remote Similarity	NPD8294	Approved
0.678	Remote Similarity	NPD8377	Approved
0.6778	Remote Similarity	NPD5360	Phase 3
0.6778	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6336	Discontinued
0.6762	Remote Similarity	NPD5210	Approved
0.6762	Remote Similarity	NPD4629	Approved
0.6752	Remote Similarity	NPD7327	Approved
0.6752	Remote Similarity	NPD7328	Approved
0.6752	Remote Similarity	NPD6313	Approved
0.6752	Remote Similarity	NPD6314	Approved
0.6739	Remote Similarity	NPD6081	Approved
0.6735	Remote Similarity	NPD4221	Approved
0.6735	Remote Similarity	NPD4223	Phase 3
0.6733	Remote Similarity	NPD7524	Approved
0.6723	Remote Similarity	NPD8379	Approved
0.6723	Remote Similarity	NPD8296	Approved
0.6723	Remote Similarity	NPD6015	Approved
0.6723	Remote Similarity	NPD8378	Approved
0.6723	Remote Similarity	NPD8380	Approved
0.6723	Remote Similarity	NPD8335	Approved
0.6723	Remote Similarity	NPD6016	Approved
0.6703	Remote Similarity	NPD3698	Phase 2
0.6702	Remote Similarity	NPD3702	Approved
0.6702	Remote Similarity	NPD7339	Approved
0.6702	Remote Similarity	NPD6942	Approved
0.67	Remote Similarity	NPD5329	Approved
0.6696	Remote Similarity	NPD4730	Approved
0.6696	Remote Similarity	NPD4729	Approved
0.6696	Remote Similarity	NPD5128	Approved
0.6695	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6635	Remote Similarity	NPD7637	Suspended
0.6635	Remote Similarity	NPD5693	Phase 1
0.6635	Remote Similarity	NPD5284	Approved
0.6635	Remote Similarity	NPD5281	Approved
0.6635	Remote Similarity	NPD6050	Approved
0.6634	Remote Similarity	NPD5279	Phase 3
0.6633	Remote Similarity	NPD4139	Approved
0.6633	Remote Similarity	NPD5369	Approved
0.6633	Remote Similarity	NPD4692	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