NPASS Compound

Structure

NPC469316 OpenBabel07101718272D 38 42 0 0 1 0 0 0 0 0999 V2000 3.6749 -0.4784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3783 2.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5144 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0260 -0.6192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8777 -1.8665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1518 -1.2129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1255 0.5905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0204 1.5459 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 -1.6918 -2.9302 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 1.0490 1.4438 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 4.0266 1.1764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3730 0.4505 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3337 2.6281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4176 0.6536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9820 0.9733 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6918 -0.9767 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5377 -2.4419 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 1.6918 -0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9767 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.2838 0.0443 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5377 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0808 -0.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 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 5.9873 3.3539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 -2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -2.4419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6356 1.6991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0097 -0.6092 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 14 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 22 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 17 1 0 0 0 0 17 1 1 1 0 0 0 17 19 1 0 0 0 0 18 33 2 0 0 0 0 18 37 1 0 0 0 0 19 23 2 0 0 0 0 20 16 1 6 0 0 0 20 37 1 0 0 0 0 21 28 1 0 0 0 0 21 30 1 0 0 0 0 22 28 1 0 0 0 0 22 34 2 0 0 0 0 23 24 1 0 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 24 35 1 6 0 0 0 25 26 1 0 0 0 0 25 36 1 6 0 0 0 26 30 1 0 0 0 0 26 32 1 0 0 0 0 27 20 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 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:	490.37
Volume:	531.888
LogP:	3.564
LogD:	3.09
LogS:	-3.82
# Rotatable Bonds:	5
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	5.137
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.151
MDCK Permeability:	1.258155498362612e-05
Pgp-inhibitor:	0.955
Pgp-substrate:	0.351
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.7
Plasma Protein Binding (PPB):	91.32467651367188%
Volume Distribution (VD):	0.916
Pgp-substrate:	3.809048652648926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.456
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.619
CYP3A4-substrate:	0.662

ADMET: Excretion

Clearance (CL):	5.748
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.82
Skin Sensitization:	0.035
Carcinogencity:	0.212
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC469316

Natural Product ID:	NPC469316
*Common Name:**	[(1S,3R)-3-[(8S,10S,11R,12S,14R)-11,12-Dihydroxy-4,4,8,10,14-Pentamethyl-3-Oxo-1,2,5,6,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-17-Yl]-1-[(2R)-3,3-Dimethyloxiran-2-Yl]Butyl] Acetate
IUPAC Name:	[(1S,3R)-3-[(8S,10S,11R,12S,14R)-11,12-dihydroxy-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-1-[(2R)-3,3-dimethyloxiran-2-yl]butyl] acetate
Synonyms:
Standard InCHIKey:	PGURRWRAZQDMEZ-LXWASEEWSA-N
Standard InCHI:	InChI=1S/C32H50O6/c1-17(16-20(37-18(2)33)27-29(5,6)38-27)19-10-14-31(8)23(19)24(35)25(36)26-30(7)13-12-22(34)28(3,4)21(30)11-15-32(26,31)9/h17,20-21,24-27,35-36H,10-16H2,1-9H3/t17-,20+,21?,24+,25+,26?,27-,30+,31+,32+/m1/s1
SMILES:	CC(CC(C1C(O1)(C)C)OC(=O)C)C2=C3C(C(C4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL102985
PubChem CID:	44335302
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	=	5.9	%	PMID[464238]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	4.0	%	PMID[464238]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	32.3	%	PMID[464238]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	116.9	%	PMID[464238]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	115.7	%	PMID[464238]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	10000.0	nM	PMID[464238]

☑ 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 NPC469316 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	247
0.1-0.2	1534
0.2-0.3	4588
0.3-0.4	11088
0.4-0.5	11083
0.5-0.6	6386
0.6-0.7	5838
0.7-0.8	1867
0.8-0.85	36
0.85-0.9	15
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC471783
0.9592	High Similarity	NPC9457
0.9468	High Similarity	NPC471777
0.9362	High Similarity	NPC473415
0.9362	High Similarity	NPC30677
0.9362	High Similarity	NPC469329
0.9362	High Similarity	NPC37787
0.9362	High Similarity	NPC180557
0.9149	High Similarity	NPC274046
0.9149	High Similarity	NPC198074
0.9091	High Similarity	NPC324001
0.9082	High Similarity	NPC469327
0.9043	High Similarity	NPC473166
0.8889	High Similarity	NPC476897
0.8866	High Similarity	NPC471822
0.8824	High Similarity	NPC473173
0.8824	High Similarity	NPC469318
0.8725	High Similarity	NPC470587
0.8687	High Similarity	NPC471784
0.8687	High Similarity	NPC303777
0.866	High Similarity	NPC240617
0.8641	High Similarity	NPC473165
0.8617	High Similarity	NPC469322
0.8617	High Similarity	NPC469314
0.8617	High Similarity	NPC241875
0.8617	High Similarity	NPC469317
0.8598	High Similarity	NPC284915
0.8557	High Similarity	NPC469315
0.8438	Intermediate Similarity	NPC229871
0.8438	Intermediate Similarity	NPC469319
0.8416	Intermediate Similarity	NPC473176
0.8286	Intermediate Similarity	NPC475176
0.8286	Intermediate Similarity	NPC473284
0.8273	Intermediate Similarity	NPC470493
0.8273	Intermediate Similarity	NPC312824
0.8273	Intermediate Similarity	NPC183580
0.8241	Intermediate Similarity	NPC470063
0.8224	Intermediate Similarity	NPC472214
0.8224	Intermediate Similarity	NPC472215
0.8214	Intermediate Similarity	NPC268530
0.8214	Intermediate Similarity	NPC154491
0.8208	Intermediate Similarity	NPC472218
0.8208	Intermediate Similarity	NPC472219
0.8208	Intermediate Similarity	NPC472217
0.82	Intermediate Similarity	NPC53565
0.8191	Intermediate Similarity	NPC86370
0.819	Intermediate Similarity	NPC472655
0.819	Intermediate Similarity	NPC475414
0.819	Intermediate Similarity	NPC173172
0.8173	Intermediate Similarity	NPC264048
0.8155	Intermediate Similarity	NPC54909
0.8155	Intermediate Similarity	NPC115899
0.8155	Intermediate Similarity	NPC233012
0.8142	Intermediate Similarity	NPC4021
0.8142	Intermediate Similarity	NPC159456
0.8131	Intermediate Similarity	NPC475065
0.8131	Intermediate Similarity	NPC472216
0.8131	Intermediate Similarity	NPC284828
0.8131	Intermediate Similarity	NPC173905
0.8131	Intermediate Similarity	NPC5475
0.8131	Intermediate Similarity	NPC41405
0.8125	Intermediate Similarity	NPC42673
0.8119	Intermediate Similarity	NPC230151
0.8113	Intermediate Similarity	NPC255387
0.8113	Intermediate Similarity	NPC301666
0.8113	Intermediate Similarity	NPC131665
0.8108	Intermediate Similarity	NPC286528
0.8108	Intermediate Similarity	NPC20302
0.8108	Intermediate Similarity	NPC140055
0.8108	Intermediate Similarity	NPC470492
0.8108	Intermediate Similarity	NPC167606
0.8081	Intermediate Similarity	NPC473167
0.8058	Intermediate Similarity	NPC473510
0.8058	Intermediate Similarity	NPC266955
0.8056	Intermediate Similarity	NPC5284
0.8053	Intermediate Similarity	NPC251226
0.8037	Intermediate Similarity	NPC469916
0.8037	Intermediate Similarity	NPC472439
0.8037	Intermediate Similarity	NPC475418
0.8037	Intermediate Similarity	NPC318363
0.8037	Intermediate Similarity	NPC473482
0.8036	Intermediate Similarity	NPC50774
0.8036	Intermediate Similarity	NPC709
0.8036	Intermediate Similarity	NPC186525
0.802	Intermediate Similarity	NPC279974
0.802	Intermediate Similarity	NPC84383
0.8018	Intermediate Similarity	NPC270929
0.8	Intermediate Similarity	NPC475050
0.8	Intermediate Similarity	NPC27918
0.8	Intermediate Similarity	NPC222153
0.7982	Intermediate Similarity	NPC475668
0.7982	Intermediate Similarity	NPC475480
0.7982	Intermediate Similarity	NPC473921
0.7981	Intermediate Similarity	NPC289670
0.798	Intermediate Similarity	NPC472307
0.7965	Intermediate Similarity	NPC230513
0.7965	Intermediate Similarity	NPC264954
0.7963	Intermediate Similarity	NPC218853
0.7963	Intermediate Similarity	NPC299590
0.7963	Intermediate Similarity	NPC154906
0.7961	Intermediate Similarity	NPC470067
0.7961	Intermediate Similarity	NPC119036
0.7961	Intermediate Similarity	NPC470068
0.7961	Intermediate Similarity	NPC470066
0.7946	Intermediate Similarity	NPC471854
0.7946	Intermediate Similarity	NPC55296
0.7944	Intermediate Similarity	NPC329048
0.7944	Intermediate Similarity	NPC67321
0.7944	Intermediate Similarity	NPC330011
0.7944	Intermediate Similarity	NPC187435
0.7944	Intermediate Similarity	NPC230541
0.7941	Intermediate Similarity	NPC7124
0.7941	Intermediate Similarity	NPC327788
0.7941	Intermediate Similarity	NPC235053
0.7938	Intermediate Similarity	NPC322159
0.7928	Intermediate Similarity	NPC67259
0.7928	Intermediate Similarity	NPC147912
0.7928	Intermediate Similarity	NPC472274
0.7925	Intermediate Similarity	NPC473175
0.7921	Intermediate Similarity	NPC174051
0.7921	Intermediate Similarity	NPC159410
0.7921	Intermediate Similarity	NPC67831
0.7921	Intermediate Similarity	NPC296164
0.7921	Intermediate Similarity	NPC87095
0.7917	Intermediate Similarity	NPC473157
0.7909	Intermediate Similarity	NPC152117
0.7909	Intermediate Similarity	NPC472002
0.7909	Intermediate Similarity	NPC234042
0.7909	Intermediate Similarity	NPC476163
0.7909	Intermediate Similarity	NPC42658
0.7905	Intermediate Similarity	NPC32577
0.7905	Intermediate Similarity	NPC473163
0.7905	Intermediate Similarity	NPC114540
0.7905	Intermediate Similarity	NPC155332
0.7905	Intermediate Similarity	NPC471119
0.7905	Intermediate Similarity	NPC296879
0.79	Intermediate Similarity	NPC189520
0.79	Intermediate Similarity	NPC262870
0.79	Intermediate Similarity	NPC235704
0.7895	Intermediate Similarity	NPC474370
0.789	Intermediate Similarity	NPC475134
0.789	Intermediate Similarity	NPC475563
0.789	Intermediate Similarity	NPC250956
0.7885	Intermediate Similarity	NPC167974
0.7885	Intermediate Similarity	NPC230546
0.7879	Intermediate Similarity	NPC250592
0.7879	Intermediate Similarity	NPC469323
0.7879	Intermediate Similarity	NPC77263
0.7876	Intermediate Similarity	NPC329736
0.787	Intermediate Similarity	NPC306265
0.787	Intermediate Similarity	NPC88701
0.7864	Intermediate Similarity	NPC470425
0.7864	Intermediate Similarity	NPC9613
0.7864	Intermediate Similarity	NPC175351
0.7864	Intermediate Similarity	NPC259788
0.7864	Intermediate Similarity	NPC151681
0.7864	Intermediate Similarity	NPC247139
0.7864	Intermediate Similarity	NPC474938
0.7864	Intermediate Similarity	NPC255589
0.7864	Intermediate Similarity	NPC121402
0.7864	Intermediate Similarity	NPC210337
0.7864	Intermediate Similarity	NPC474785
0.7864	Intermediate Similarity	NPC224356
0.7864	Intermediate Similarity	NPC132753
0.7863	Intermediate Similarity	NPC120994
0.7863	Intermediate Similarity	NPC203702
0.7857	Intermediate Similarity	NPC138756
0.7857	Intermediate Similarity	NPC64318
0.7857	Intermediate Similarity	NPC179626
0.785	Intermediate Similarity	NPC477877
0.785	Intermediate Similarity	NPC323834
0.7843	Intermediate Similarity	NPC473170
0.7843	Intermediate Similarity	NPC134067
0.7843	Intermediate Similarity	NPC32118
0.7838	Intermediate Similarity	NPC250109
0.7838	Intermediate Similarity	NPC122056
0.7838	Intermediate Similarity	NPC317210
0.7838	Intermediate Similarity	NPC255017
0.783	Intermediate Similarity	NPC474822
0.783	Intermediate Similarity	NPC72151
0.783	Intermediate Similarity	NPC471005
0.783	Intermediate Similarity	NPC218513
0.783	Intermediate Similarity	NPC90177
0.783	Intermediate Similarity	NPC55954
0.783	Intermediate Similarity	NPC478057
0.783	Intermediate Similarity	NPC112009
0.783	Intermediate Similarity	NPC180204
0.7826	Intermediate Similarity	NPC67569
0.7822	Intermediate Similarity	NPC74855
0.7822	Intermediate Similarity	NPC136313
0.7822	Intermediate Similarity	NPC275809
0.7822	Intermediate Similarity	NPC170220
0.7822	Intermediate Similarity	NPC133579
0.7822	Intermediate Similarity	NPC107674
0.7822	Intermediate Similarity	NPC86368
0.7822	Intermediate Similarity	NPC307335
0.7822	Intermediate Similarity	NPC141497
0.7822	Intermediate Similarity	NPC474806
0.7818	Intermediate Similarity	NPC474846
0.7818	Intermediate Similarity	NPC469655

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 NPC469316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	1854
0.2-0.3	3748
0.3-0.4	2214
0.4-0.5	663
0.5-0.6	255
0.6-0.7	188
0.7-0.8	15
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
0.8108	Intermediate Similarity	NPD7115	Discovery
0.7963	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD7748	Approved
0.7568	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7639	Approved
0.7547	Intermediate Similarity	NPD7640	Approved
0.7477	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD6399	Phase 3
0.7453	Intermediate Similarity	NPD7638	Approved
0.7453	Intermediate Similarity	NPD4225	Approved
0.7434	Intermediate Similarity	NPD8297	Approved
0.7407	Intermediate Similarity	NPD7632	Discontinued
0.7379	Intermediate Similarity	NPD8035	Phase 2
0.7379	Intermediate Similarity	NPD7515	Phase 2
0.7379	Intermediate Similarity	NPD8034	Phase 2
0.7364	Intermediate Similarity	NPD6402	Approved
0.7364	Intermediate Similarity	NPD6675	Approved
0.7364	Intermediate Similarity	NPD7128	Approved
0.7364	Intermediate Similarity	NPD5739	Approved
0.7358	Intermediate Similarity	NPD7902	Approved
0.73	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6881	Approved
0.7232	Intermediate Similarity	NPD7320	Approved
0.7232	Intermediate Similarity	NPD6899	Approved
0.72	Intermediate Similarity	NPD4786	Approved
0.7196	Intermediate Similarity	NPD6084	Phase 2
0.7196	Intermediate Similarity	NPD6083	Phase 2
0.7193	Intermediate Similarity	NPD8130	Phase 1
0.7172	Intermediate Similarity	NPD3667	Approved
0.7168	Intermediate Similarity	NPD6373	Approved
0.7168	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD5697	Approved
0.7105	Intermediate Similarity	NPD6883	Approved
0.7105	Intermediate Similarity	NPD7290	Approved
0.7105	Intermediate Similarity	NPD7102	Approved
0.7083	Intermediate Similarity	NPD6117	Approved
0.708	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7900	Approved
0.7059	Intermediate Similarity	NPD3618	Phase 1
0.7043	Intermediate Similarity	NPD6869	Approved
0.7043	Intermediate Similarity	NPD6650	Approved
0.7043	Intermediate Similarity	NPD6847	Approved
0.7043	Intermediate Similarity	NPD6649	Approved
0.7043	Intermediate Similarity	NPD6617	Approved
0.7034	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5328	Approved
0.7018	Intermediate Similarity	NPD6012	Approved
0.7018	Intermediate Similarity	NPD6013	Approved
0.7018	Intermediate Similarity	NPD6014	Approved
0.701	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD4159	Approved
0.6992	Remote Similarity	NPD7507	Approved
0.6983	Remote Similarity	NPD6882	Approved
0.6939	Remote Similarity	NPD6697	Approved
0.6939	Remote Similarity	NPD6118	Approved
0.6939	Remote Similarity	NPD6115	Approved
0.6939	Remote Similarity	NPD6114	Approved
0.6937	Remote Similarity	NPD5211	Phase 2
0.693	Remote Similarity	NPD6011	Approved
0.693	Remote Similarity	NPD6686	Approved
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.6903	Remote Similarity	NPD6008	Approved
0.6897	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7334	Approved
0.6893	Remote Similarity	NPD7146	Approved
0.6893	Remote Similarity	NPD7521	Approved
0.6893	Remote Similarity	NPD5330	Approved
0.6893	Remote Similarity	NPD6684	Approved
0.6893	Remote Similarity	NPD6409	Approved
0.6887	Remote Similarity	NPD6079	Approved
0.6881	Remote Similarity	NPD4755	Approved
0.6875	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6319	Approved
0.6852	Remote Similarity	NPD5695	Phase 3
0.6852	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5344	Discontinued
0.6842	Remote Similarity	NPD6412	Phase 2
0.6827	Remote Similarity	NPD7524	Approved
0.6825	Remote Similarity	NPD7319	Approved
0.6822	Remote Similarity	NPD4202	Approved
0.6818	Remote Similarity	NPD5696	Approved
0.6814	Remote Similarity	NPD5141	Approved
0.6803	Remote Similarity	NPD8033	Approved
0.68	Remote Similarity	NPD7525	Registered
0.6777	Remote Similarity	NPD7516	Approved
0.6765	Remote Similarity	NPD7154	Phase 3
0.6762	Remote Similarity	NPD6672	Approved
0.6762	Remote Similarity	NPD6903	Approved
0.6762	Remote Similarity	NPD5737	Approved
0.6757	Remote Similarity	NPD4700	Approved
0.6757	Remote Similarity	NPD5286	Approved
0.6757	Remote Similarity	NPD4696	Approved
0.6757	Remote Similarity	NPD5285	Approved
0.6746	Remote Similarity	NPD7736	Approved
0.6729	Remote Similarity	NPD7637	Suspended
0.6729	Remote Similarity	NPD6411	Approved
0.6721	Remote Similarity	NPD8377	Approved
0.6721	Remote Similarity	NPD8294	Approved
0.6699	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD3665	Phase 1
0.6699	Remote Similarity	NPD3133	Approved
0.6699	Remote Similarity	NPD3666	Approved
0.6698	Remote Similarity	NPD4753	Phase 2
0.6694	Remote Similarity	NPD8328	Phase 3
0.6694	Remote Similarity	NPD7327	Approved
0.6694	Remote Similarity	NPD7328	Approved
0.6694	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.664	Remote Similarity	NPD7492	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6637	Remote Similarity	NPD4633	Approved
0.6637	Remote Similarity	NPD5225	Approved
0.6637	Remote Similarity	NPD5224	Approved
0.6637	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD5222	Approved
0.6636	Remote Similarity	NPD6698	Approved
0.6636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD46	Approved
0.6636	Remote Similarity	NPD4697	Phase 3
0.6632	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6009	Approved
0.6602	Remote Similarity	NPD5362	Discontinued
0.6602	Remote Similarity	NPD4788	Approved
0.66	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6616	Approved
0.6585	Remote Similarity	NPD6059	Approved
0.6585	Remote Similarity	NPD6054	Approved
0.6579	Remote Similarity	NPD5174	Approved
0.6579	Remote Similarity	NPD5175	Approved
0.6577	Remote Similarity	NPD5173	Approved
0.6571	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6098	Approved
0.6571	Remote Similarity	NPD4519	Discontinued
0.6571	Remote Similarity	NPD4623	Approved
0.6557	Remote Similarity	NPD6335	Approved
0.6549	Remote Similarity	NPD5223	Approved
0.6542	Remote Similarity	NPD6101	Approved
0.6542	Remote Similarity	NPD6673	Approved
0.6542	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6080	Approved
0.6542	Remote Similarity	NPD6904	Approved
0.6535	Remote Similarity	NPD7078	Approved
0.6535	Remote Similarity	NPD7645	Phase 2
0.6532	Remote Similarity	NPD6909	Approved
0.6532	Remote Similarity	NPD6908	Approved
0.6532	Remote Similarity	NPD5983	Phase 2
0.6529	Remote Similarity	NPD6868	Approved
0.6525	Remote Similarity	NPD4634	Approved
0.6509	Remote Similarity	NPD3573	Approved
0.6505	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5777	Approved
0.648	Remote Similarity	NPD6370	Approved
0.6476	Remote Similarity	NPD1694	Approved
0.6475	Remote Similarity	NPD6317	Approved
0.6466	Remote Similarity	NPD4767	Approved
0.6466	Remote Similarity	NPD4768	Approved
0.6465	Remote Similarity	NPD3703	Phase 2
0.646	Remote Similarity	NPD6648	Approved
0.6458	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6336	Discontinued
0.6455	Remote Similarity	NPD6001	Approved
0.6442	Remote Similarity	NPD6695	Phase 3
0.6436	Remote Similarity	NPD3617	Approved
0.6435	Remote Similarity	NPD4754	Approved
0.6423	Remote Similarity	NPD6313	Approved
0.6423	Remote Similarity	NPD6314	Approved
0.6422	Remote Similarity	NPD5693	Phase 1
0.6422	Remote Similarity	NPD7983	Approved
0.64	Remote Similarity	NPD6921	Approved
0.64	Remote Similarity	NPD8513	Phase 3
0.64	Remote Similarity	NPD6015	Approved
0.64	Remote Similarity	NPD6016	Approved
0.64	Remote Similarity	NPD8515	Approved
0.64	Remote Similarity	NPD8517	Approved
0.64	Remote Similarity	NPD8516	Approved
0.6396	Remote Similarity	NPD5210	Approved
0.6396	Remote Similarity	NPD4629	Approved
0.6392	Remote Similarity	NPD4244	Approved
0.6392	Remote Similarity	NPD4245	Approved
0.6389	Remote Similarity	NPD6051	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