NPASS Compound

Structure

CID236112 OpenBabel06191716032D 32 35 0 0 1 0 0 0 0 0999 V2000 4.1450 -8.0458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6869 -7.3588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3516 -6.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8439 1.4991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -3.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 -1.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8936 -5.5783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4969 -4.6880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3786 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5335 0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9129 -2.4367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9126 -1.4617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5343 -2.4377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3794 -2.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0388 -4.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7176 -7.2572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3209 -6.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8442 0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0695 -3.8994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3788 -0.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0693 -2.9248 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2239 -1.4622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5340 -1.4627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9756 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 4.2242 -2.4372 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6890 -0.9751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4355 -4.8912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8657 -1.4757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8662 0.4996 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 2 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 26 1 0 0 0 0 15 29 1 0 0 0 0 16 20 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 19 4 1 1 0 0 0 19 22 1 0 0 0 0 19 27 1 0 0 0 0 20 8 1 6 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 21 25 1 0 0 0 0 22 29 1 6 0 0 0 23 28 1 6 0 0 0 24 28 1 6 0 0 0 25 29 1 6 0 0 0 26 27 1 0 0 0 0 26 31 1 1 0 0 0 27 32 1 6 0 0 0 28 5 1 6 0 0 0 29 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.36
Volume:	497.012
LogP:	5.794
LogD:	5.156
LogS:	-5.95
# Rotatable Bonds:	6
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	5.057
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.762
MDCK Permeability:	1.4403728528122883e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.752

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	96.56520080566406%
Volume Distribution (VD):	0.958
Pgp-substrate:	1.98427414894104%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.263
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.11
CYP2C9-substrate:	0.277
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.792
CYP3A4-inhibitor:	0.763
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	5.283
Half-life (T1/2):	0.122

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.263
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.092
Carcinogencity:	0.018
Eye Corrosion:	0.036
Eye Irritation:	0.143
Respiratory Toxicity:	0.637

Download Data

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

Natural Product: NPC236112

Natural Product ID:	NPC236112
*Common Name:**	Fruticoside A
IUPAC Name:	(2R,3R,4S,5S,9R,10S,13R,14R,17R)-17-[(2R)-1-hydroxy-6-methyl-5-methylideneheptan-2-yl]-4,10,13-trimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-2,3-diol
Synonyms:	Fruticoside A
Standard InCHIKey:	OJCFPYLTKWNLCE-CBUQHMQYSA-N
Standard InCHI:	InChI=1S/C29H48O3/c1-17(2)18(3)7-8-20(16-30)23-11-12-24-21-9-10-22-19(4)27(32)26(31)15-29(22,6)25(21)13-14-28(23,24)5/h9,17,19-20,22-27,30-32H,3,7-8,10-16H2,1-2,4-6H3/t19-,20-,22-,23+,24-,25-,26+,27+,28+,29-/m0/s1
SMILES:	OC[C@@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)C[C@@H](O)[C@@H]([C@H]2C)O)CCC(=C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782590
PubChem CID:	53355688
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001104] Trihydroxy bile acids, alcohols and derivatives

*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
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	root	n.a.	PMID[21428418]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	roots	Xishuangbanna of Yunnan Province, China	n.a.	PMID[21428418]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3000.0	nM	PMID[513039]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	18500.0	nM	PMID[513039]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	15700.0	nM	PMID[513039]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15400.0	nM	PMID[513039]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	18400.0	nM	PMID[513039]

☑ 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 NPC236112 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	156
0.1-0.2	1377
0.2-0.3	6451
0.3-0.4	16074
0.4-0.5	7331
0.5-0.6	5209
0.6-0.7	4307
0.7-0.8	1358
0.8-0.85	247
0.85-0.9	141
0.9-0.95	44
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC474531
0.9481	High Similarity	NPC30166
0.9474	High Similarity	NPC13554
0.9459	High Similarity	NPC189883
0.9359	High Similarity	NPC207013
0.9359	High Similarity	NPC317458
0.9342	High Similarity	NPC328714
0.9342	High Similarity	NPC1319
0.9333	High Similarity	NPC214570
0.9324	High Similarity	NPC471723
0.9324	High Similarity	NPC257347
0.9324	High Similarity	NPC141071
0.925	High Similarity	NPC94462
0.9211	High Similarity	NPC167037
0.9211	High Similarity	NPC285761
0.9211	High Similarity	NPC138621
0.9211	High Similarity	NPC6978
0.9211	High Similarity	NPC275910
0.9211	High Similarity	NPC244385
0.92	High Similarity	NPC321016
0.92	High Similarity	NPC240604
0.92	High Similarity	NPC129165
0.92	High Similarity	NPC107059
0.92	High Similarity	NPC300324
0.92	High Similarity	NPC134330
0.92	High Similarity	NPC321381
0.92	High Similarity	NPC237460
0.92	High Similarity	NPC73875
0.92	High Similarity	NPC202642
0.92	High Similarity	NPC46160
0.9103	High Similarity	NPC6707
0.9091	High Similarity	NPC273410
0.9091	High Similarity	NPC30986
0.9091	High Similarity	NPC80530
0.9091	High Similarity	NPC209430
0.9079	High Similarity	NPC198968
0.9079	High Similarity	NPC318495
0.9079	High Similarity	NPC155986
0.9067	High Similarity	NPC230301
0.9067	High Similarity	NPC304309
0.9067	High Similarity	NPC28657
0.9067	High Similarity	NPC288035
0.9067	High Similarity	NPC477923
0.9067	High Similarity	NPC136188
0.9067	High Similarity	NPC162742
0.9067	High Similarity	NPC134847
0.9067	High Similarity	NPC66566
0.9067	High Similarity	NPC285893
0.9067	High Similarity	NPC118508
0.9067	High Similarity	NPC22105
0.9067	High Similarity	NPC322353
0.9067	High Similarity	NPC121744
0.9024	High Similarity	NPC133588
0.9012	High Similarity	NPC125399
0.9012	High Similarity	NPC477604
0.9012	High Similarity	NPC269058
0.9012	High Similarity	NPC71520
0.9	High Similarity	NPC185568
0.8987	High Similarity	NPC470049
0.8974	High Similarity	NPC322313
0.8974	High Similarity	NPC102253
0.8974	High Similarity	NPC236237
0.8974	High Similarity	NPC22403
0.8961	High Similarity	NPC477522
0.8961	High Similarity	NPC102708
0.8961	High Similarity	NPC85346
0.8961	High Similarity	NPC473943
0.8961	High Similarity	NPC302041
0.8961	High Similarity	NPC186191
0.8961	High Similarity	NPC474216
0.8961	High Similarity	NPC87604
0.8961	High Similarity	NPC205455
0.8961	High Similarity	NPC65897
0.8947	High Similarity	NPC113733
0.8947	High Similarity	NPC470362
0.8947	High Similarity	NPC91573
0.8916	High Similarity	NPC105495
0.8902	High Similarity	NPC470620
0.8875	High Similarity	NPC474634
0.8861	High Similarity	NPC70927
0.8861	High Similarity	NPC470383
0.8846	High Similarity	NPC28862
0.8846	High Similarity	NPC47982
0.8846	High Similarity	NPC109546
0.8846	High Similarity	NPC81306
0.8846	High Similarity	NPC143182
0.8846	High Similarity	NPC84694
0.8831	High Similarity	NPC130136
0.8831	High Similarity	NPC477924
0.8831	High Similarity	NPC34019
0.88	High Similarity	NPC182717
0.88	High Similarity	NPC474140
0.88	High Similarity	NPC201373
0.8795	High Similarity	NPC474668
0.8765	High Similarity	NPC478102
0.8765	High Similarity	NPC470077
0.8765	High Similarity	NPC209802
0.8765	High Similarity	NPC124172
0.875	High Similarity	NPC7988
0.875	High Similarity	NPC20853
0.875	High Similarity	NPC248886
0.875	High Similarity	NPC47763
0.875	High Similarity	NPC201852
0.875	High Similarity	NPC87489
0.875	High Similarity	NPC296701
0.875	High Similarity	NPC49964
0.875	High Similarity	NPC218616
0.875	High Similarity	NPC202389
0.875	High Similarity	NPC101462
0.8734	High Similarity	NPC209944
0.8734	High Similarity	NPC234193
0.8734	High Similarity	NPC26117
0.8734	High Similarity	NPC164840
0.8734	High Similarity	NPC287749
0.8734	High Similarity	NPC241290
0.8718	High Similarity	NPC477514
0.8718	High Similarity	NPC307965
0.8718	High Similarity	NPC18603
0.8718	High Similarity	NPC76931
0.8718	High Similarity	NPC318136
0.8718	High Similarity	NPC312328
0.8706	High Similarity	NPC189520
0.8701	High Similarity	NPC244488
0.8701	High Similarity	NPC274079
0.8701	High Similarity	NPC247325
0.8701	High Similarity	NPC477925
0.8701	High Similarity	NPC96319
0.869	High Similarity	NPC470361
0.869	High Similarity	NPC477606
0.8684	High Similarity	NPC469534
0.8684	High Similarity	NPC469593
0.8684	High Similarity	NPC243342
0.8684	High Similarity	NPC91858
0.8684	High Similarity	NPC100334
0.8684	High Similarity	NPC477138
0.8684	High Similarity	NPC469533
0.8675	High Similarity	NPC474657
0.8675	High Similarity	NPC186145
0.8667	High Similarity	NPC167706
0.8667	High Similarity	NPC111234
0.8659	High Similarity	NPC318390
0.8642	High Similarity	NPC113978
0.8642	High Similarity	NPC477818
0.8642	High Similarity	NPC159168
0.8642	High Similarity	NPC253402
0.8642	High Similarity	NPC110778
0.8625	High Similarity	NPC474759
0.8625	High Similarity	NPC264245
0.8625	High Similarity	NPC47761
0.8625	High Similarity	NPC474683
0.8625	High Similarity	NPC474752
0.8625	High Similarity	NPC7505
0.8625	High Similarity	NPC209620
0.8625	High Similarity	NPC474731
0.8625	High Similarity	NPC23852
0.8625	High Similarity	NPC82986
0.8608	High Similarity	NPC472463
0.859	High Similarity	NPC471798
0.859	High Similarity	NPC34177
0.859	High Similarity	NPC40394
0.859	High Similarity	NPC90979
0.859	High Similarity	NPC472805
0.859	High Similarity	NPC101475
0.859	High Similarity	NPC157996
0.8588	High Similarity	NPC291484
0.8588	High Similarity	NPC3345
0.8588	High Similarity	NPC11216
0.8588	High Similarity	NPC329596
0.8588	High Similarity	NPC80561
0.8588	High Similarity	NPC204188
0.8571	High Similarity	NPC291503
0.8571	High Similarity	NPC70982
0.8571	High Similarity	NPC212879
0.8571	High Similarity	NPC3403
0.8571	High Similarity	NPC104387
0.8571	High Similarity	NPC240235
0.8571	High Similarity	NPC231256
0.8571	High Similarity	NPC67872
0.8571	High Similarity	NPC475664
0.8571	High Similarity	NPC185536
0.8571	High Similarity	NPC230704
0.8571	High Similarity	NPC280556
0.8571	High Similarity	NPC178383
0.8554	High Similarity	NPC474970
0.8554	High Similarity	NPC24277
0.8554	High Similarity	NPC6391
0.8554	High Similarity	NPC261266
0.8553	High Similarity	NPC471799
0.8537	High Similarity	NPC474047
0.8537	High Similarity	NPC231310
0.8537	High Similarity	NPC238992
0.8537	High Similarity	NPC205845
0.8533	High Similarity	NPC45296
0.8519	High Similarity	NPC470614
0.8519	High Similarity	NPC1272
0.8519	High Similarity	NPC477599
0.8519	High Similarity	NPC189972
0.8519	High Similarity	NPC50964
0.8519	High Similarity	NPC5985
0.8514	High Similarity	NPC160209

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 NPC236112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1649
0.2-0.3	4475
0.3-0.4	2067
0.4-0.5	396
0.5-0.6	139
0.6-0.7	170
0.7-0.8	85
0.8-0.85	13
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9067	High Similarity	NPD7339	Approved
0.9067	High Similarity	NPD6942	Approved
0.8974	High Similarity	NPD7525	Registered
0.8701	High Similarity	NPD3701	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6933	Approved
0.8375	Intermediate Similarity	NPD7645	Phase 2
0.8313	Intermediate Similarity	NPD4786	Approved
0.8256	Intermediate Similarity	NPD5328	Approved
0.8205	Intermediate Similarity	NPD6926	Approved
0.8205	Intermediate Similarity	NPD6924	Approved
0.8182	Intermediate Similarity	NPD4243	Approved
0.8118	Intermediate Similarity	NPD3618	Phase 1
0.8072	Intermediate Similarity	NPD3667	Approved
0.8068	Intermediate Similarity	NPD6079	Approved
0.7975	Intermediate Similarity	NPD4784	Approved
0.7975	Intermediate Similarity	NPD4785	Approved
0.7949	Intermediate Similarity	NPD7150	Approved
0.7949	Intermediate Similarity	NPD7151	Approved
0.7949	Intermediate Similarity	NPD7152	Approved
0.7922	Intermediate Similarity	NPD6922	Approved
0.7922	Intermediate Similarity	NPD6923	Approved
0.7831	Intermediate Similarity	NPD4748	Discontinued
0.7821	Intermediate Similarity	NPD7143	Approved
0.7821	Intermediate Similarity	NPD7144	Approved
0.7816	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4202	Approved
0.7711	Intermediate Similarity	NPD6929	Approved
0.7692	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3665	Phase 1
0.7674	Intermediate Similarity	NPD3666	Approved
0.7674	Intermediate Similarity	NPD3133	Approved
0.7654	Intermediate Similarity	NPD5275	Approved
0.7654	Intermediate Similarity	NPD4190	Phase 3
0.7619	Intermediate Similarity	NPD7509	Discontinued
0.7619	Intermediate Similarity	NPD6931	Approved
0.7619	Intermediate Similarity	NPD6930	Phase 2
0.7614	Intermediate Similarity	NPD7524	Approved
0.7586	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4697	Phase 3
0.7527	Intermediate Similarity	NPD5221	Approved
0.7527	Intermediate Similarity	NPD5222	Approved
0.7527	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4195	Approved
0.747	Intermediate Similarity	NPD6925	Approved
0.747	Intermediate Similarity	NPD6932	Approved
0.747	Intermediate Similarity	NPD5776	Phase 2
0.7447	Intermediate Similarity	NPD5173	Approved
0.7447	Intermediate Similarity	NPD4755	Approved
0.7391	Intermediate Similarity	NPD6399	Phase 3
0.7381	Intermediate Similarity	NPD7145	Approved
0.7356	Intermediate Similarity	NPD6695	Phase 3
0.7303	Intermediate Similarity	NPD5279	Phase 3
0.7294	Intermediate Similarity	NPD6683	Phase 2
0.7292	Intermediate Similarity	NPD4700	Approved
0.7292	Intermediate Similarity	NPD5285	Approved
0.7292	Intermediate Similarity	NPD4696	Approved
0.7292	Intermediate Similarity	NPD5286	Approved
0.7283	Intermediate Similarity	NPD7515	Phase 2
0.7273	Intermediate Similarity	NPD3668	Phase 3
0.7273	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4753	Phase 2
0.7241	Intermediate Similarity	NPD4221	Approved
0.7241	Intermediate Similarity	NPD4223	Phase 3
0.7229	Intermediate Similarity	NPD8264	Approved
0.7216	Intermediate Similarity	NPD5223	Approved
0.7209	Intermediate Similarity	NPD7514	Phase 3
0.7191	Intermediate Similarity	NPD5329	Approved
0.7191	Intermediate Similarity	NPD6893	Approved
0.7188	Intermediate Similarity	NPD5290	Discontinued
0.7188	Intermediate Similarity	NPD7638	Approved
0.7176	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5224	Approved
0.7143	Intermediate Similarity	NPD5211	Phase 2
0.7143	Intermediate Similarity	NPD4633	Approved
0.7143	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD5225	Approved
0.7126	Intermediate Similarity	NPD6902	Approved
0.7113	Intermediate Similarity	NPD7640	Approved
0.7113	Intermediate Similarity	NPD7639	Approved
0.71	Intermediate Similarity	NPD5739	Approved
0.71	Intermediate Similarity	NPD7128	Approved
0.71	Intermediate Similarity	NPD6675	Approved
0.71	Intermediate Similarity	NPD6402	Approved
0.7079	Intermediate Similarity	NPD4197	Approved
0.7071	Intermediate Similarity	NPD5174	Approved
0.7071	Intermediate Similarity	NPD4754	Approved
0.7071	Intermediate Similarity	NPD5175	Approved
0.7041	Intermediate Similarity	NPD4159	Approved
0.7033	Intermediate Similarity	NPD7750	Discontinued
0.7011	Intermediate Similarity	NPD7332	Phase 2
0.7	Intermediate Similarity	NPD5141	Approved
0.699	Remote Similarity	NPD4634	Approved
0.6966	Remote Similarity	NPD4788	Approved
0.6961	Remote Similarity	NPD7320	Approved
0.6961	Remote Similarity	NPD6899	Approved
0.6961	Remote Similarity	NPD6881	Approved
0.6951	Remote Similarity	NPD4787	Phase 1
0.6947	Remote Similarity	NPD7748	Approved
0.6932	Remote Similarity	NPD6898	Phase 1
0.6931	Remote Similarity	NPD4768	Approved
0.6931	Remote Similarity	NPD4767	Approved
0.6923	Remote Similarity	NPD6409	Approved
0.6923	Remote Similarity	NPD4688	Approved
0.6923	Remote Similarity	NPD5330	Approved
0.6923	Remote Similarity	NPD7334	Approved
0.6923	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6684	Approved
0.6923	Remote Similarity	NPD7146	Approved
0.6923	Remote Similarity	NPD4138	Approved
0.6923	Remote Similarity	NPD4689	Approved
0.6923	Remote Similarity	NPD4693	Phase 3
0.6923	Remote Similarity	NPD4690	Approved
0.6923	Remote Similarity	NPD7521	Approved
0.6923	Remote Similarity	NPD5205	Approved
0.6915	Remote Similarity	NPD8034	Phase 2
0.6915	Remote Similarity	NPD8035	Phase 2
0.6907	Remote Similarity	NPD6083	Phase 2
0.6907	Remote Similarity	NPD6084	Phase 2
0.6893	Remote Similarity	NPD6373	Approved
0.6893	Remote Similarity	NPD6372	Approved
0.6882	Remote Similarity	NPD6051	Approved
0.6875	Remote Similarity	NPD5210	Approved
0.6875	Remote Similarity	NPD4629	Approved
0.6867	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5701	Approved
0.6863	Remote Similarity	NPD5697	Approved
0.6857	Remote Similarity	NPD8297	Approved
0.6827	Remote Similarity	NPD7290	Approved
0.6827	Remote Similarity	NPD6883	Approved
0.6827	Remote Similarity	NPD7102	Approved
0.6796	Remote Similarity	NPD6011	Approved
0.6796	Remote Similarity	NPD4730	Approved
0.6796	Remote Similarity	NPD4729	Approved
0.6796	Remote Similarity	NPD5128	Approved
0.6796	Remote Similarity	NPD5168	Approved
0.6792	Remote Similarity	NPD4632	Approved
0.6782	Remote Similarity	NPD3617	Approved
0.6774	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6903	Approved
0.6774	Remote Similarity	NPD4722	Approved
0.6774	Remote Similarity	NPD6672	Approved
0.6774	Remote Similarity	NPD5737	Approved
0.6774	Remote Similarity	NPD4723	Approved
0.6762	Remote Similarity	NPD6869	Approved
0.6762	Remote Similarity	NPD6649	Approved
0.6762	Remote Similarity	NPD6847	Approved
0.6762	Remote Similarity	NPD8130	Phase 1
0.6762	Remote Similarity	NPD6650	Approved
0.6762	Remote Similarity	NPD6617	Approved
0.6762	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7115	Discovery
0.6744	Remote Similarity	NPD6117	Approved
0.6739	Remote Similarity	NPD4694	Approved
0.6739	Remote Similarity	NPD5690	Phase 2
0.6739	Remote Similarity	NPD5280	Approved
0.6737	Remote Similarity	NPD7087	Discontinued
0.6735	Remote Similarity	NPD7902	Approved
0.6731	Remote Similarity	NPD6012	Approved
0.6731	Remote Similarity	NPD6014	Approved
0.6731	Remote Similarity	NPD6013	Approved
0.6706	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6412	Phase 2
0.6698	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD7516	Approved
0.6627	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5215	Approved
0.6604	Remote Similarity	NPD5217	Approved
0.6604	Remote Similarity	NPD5127	Approved
0.6604	Remote Similarity	NPD5216	Approved
0.6591	Remote Similarity	NPD6118	Approved
0.6591	Remote Similarity	NPD6114	Approved
0.6591	Remote Similarity	NPD6697	Approved
0.6591	Remote Similarity	NPD6115	Approved
0.6582	Remote Similarity	NPD368	Approved
0.6559	Remote Similarity	NPD6098	Approved
0.6556	Remote Similarity	NPD4139	Approved
0.6556	Remote Similarity	NPD4692	Approved
0.6548	Remote Similarity	NPD4747	Approved
0.6545	Remote Similarity	NPD7327	Approved
0.6545	Remote Similarity	NPD7328	Approved
0.6531	Remote Similarity	NPD5695	Phase 3
0.6531	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6868	Approved
0.65	Remote Similarity	NPD5696	Approved
0.6471	Remote Similarity	NPD7632	Discontinued
0.6455	Remote Similarity	NPD6009	Approved
0.6444	Remote Similarity	NPD4695	Discontinued
0.6437	Remote Similarity	NPD3703	Phase 2

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