NPASS Compound

Structure

NPC257457 OpenBabel07101718222D 40 43 0 0 1 0 0 0 0 0999 V2000 1.4164 4.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7776 1.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8266 1.3524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 1.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 2.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3946 4.0247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0345 2.3305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0637 4.7679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7036 3.0737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 10 11 1 0 0 0 0 10 18 2 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 15 29 1 0 0 0 0 16 24 1 0 0 0 0 16 30 1 0 0 0 0 17 33 2 0 0 0 0 17 40 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 31 1 6 0 0 0 20 26 1 0 0 0 0 20 34 1 6 0 0 0 21 25 1 0 0 0 0 21 35 1 1 0 0 0 22 29 1 1 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 23 36 2 0 0 0 0 24 31 1 0 0 0 0 24 37 2 0 0 0 0 25 30 1 6 0 0 0 25 32 1 0 0 0 0 26 28 1 0 0 0 0 26 38 1 1 0 0 0 27 40 1 0 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 31 8 1 6 0 0 0 32 9 1 6 0 0 0 32 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.33
Volume:	584.942
LogP:	3.108
LogD:	2.972
LogS:	-4.463
# Rotatable Bonds:	6
TPSA:	141.36
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	5.434
Fsp3:	0.781
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:	-5.029
MDCK Permeability:	1.407866511726752e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.183
Human Intestinal Absorption (HIA):	0.094
20% Bioavailability (F20%):	0.201
30% Bioavailability (F30%):	0.104

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.571
Plasma Protein Binding (PPB):	67.94232177734375%
Volume Distribution (VD):	0.544
Pgp-substrate:	22.712038040161133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.738
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.55
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.746
CYP3A4-substrate:	0.613

ADMET: Excretion

Clearance (CL):	3.05
Half-life (T1/2):	0.485

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.096
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.637
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.234
Carcinogencity:	0.845
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC257457

Natural Product ID:	NPC257457
*Common Name:**	25-Acetylcucurbitacin F
IUPAC Name:	[(E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-3-en-2-yl] acetate
Synonyms:	25-Acetylcucurbitacin F; 25-O-Acetylcucurbitacin F
Standard InCHIKey:	LMJMTWXDWFWZHV-OBTWUPKTSA-N
Standard InCHI:	InChI=1S/C32H48O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25-26,34-35,38-39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,26-,29+,30-,31+,32+/m1/s1
SMILES:	CC(=O)OC(/C=C/C(=O)[C@@]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1C[C@H](O)[C@H](C2(C)C)O)C)C)(O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447610
PubChem CID:	14165733
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO10443	Sloanea zuliaensis	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640532]
NPO32449	eleaocarpus chinensis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22239601]
NPO10443	Sloanea zuliaensis	Species	Elaeocarpaceae	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
GI50	3
IC50	1

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	110.0	nM	PMID[495179]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	65.0	nM	PMID[495179]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	87.0	nM	PMID[495179]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	540.0	nM	PMID[495180]

☑ 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 NPC257457 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	234
0.1-0.2	1280
0.2-0.3	3912
0.3-0.4	7686
0.4-0.5	12866
0.5-0.6	6453
0.6-0.7	6673
0.7-0.8	3122
0.8-0.85	396
0.85-0.9	61
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC311554
0.9725	High Similarity	NPC471854
0.9537	High Similarity	NPC100267
0.9537	High Similarity	NPC475524
0.9279	High Similarity	NPC148458
0.9196	High Similarity	NPC239273
0.9182	High Similarity	NPC221144
0.9083	High Similarity	NPC214644
0.9074	High Similarity	NPC475294
0.9009	High Similarity	NPC280782
0.9	High Similarity	NPC471855
0.886	High Similarity	NPC476965
0.886	High Similarity	NPC470959
0.885	High Similarity	NPC67259
0.885	High Similarity	NPC147912
0.8839	High Similarity	NPC264634
0.8839	High Similarity	NPC147180
0.8833	High Similarity	NPC471407
0.8803	High Similarity	NPC222688
0.8761	High Similarity	NPC250109
0.8761	High Similarity	NPC962
0.8729	High Similarity	NPC473979
0.8727	High Similarity	NPC44063
0.8707	High Similarity	NPC264954
0.8707	High Similarity	NPC475041
0.8678	High Similarity	NPC231529
0.8673	High Similarity	NPC71348
0.8667	High Similarity	NPC470882
0.8661	High Similarity	NPC473627
0.8649	High Similarity	NPC472825
0.8644	High Similarity	NPC269642
0.8632	High Similarity	NPC109973
0.8632	High Similarity	NPC476961
0.8632	High Similarity	NPC474370
0.8624	High Similarity	NPC311612
0.8621	High Similarity	NPC329736
0.8609	High Similarity	NPC266728
0.8609	High Similarity	NPC49492
0.8609	High Similarity	NPC270958
0.8596	High Similarity	NPC108721
0.8596	High Similarity	NPC73300
0.8584	High Similarity	NPC43775
0.8583	High Similarity	NPC15095
0.8583	High Similarity	NPC473635
0.8571	High Similarity	NPC11895
0.8571	High Similarity	NPC2766
0.8559	High Similarity	NPC185
0.8547	High Similarity	NPC61520
0.8547	High Similarity	NPC473270
0.8547	High Similarity	NPC5292
0.8534	High Similarity	NPC140055
0.8534	High Similarity	NPC284068
0.8534	High Similarity	NPC167606
0.8534	High Similarity	NPC286528
0.8534	High Similarity	NPC20302
0.8534	High Similarity	NPC470492
0.8532	High Similarity	NPC87351
0.8532	High Similarity	NPC477915
0.8525	High Similarity	NPC35109
0.8512	High Similarity	NPC473265
0.85	High Similarity	NPC81736
0.85	High Similarity	NPC172154
0.85	High Similarity	NPC473255
0.8496	Intermediate Similarity	NPC37116
0.8487	Intermediate Similarity	NPC88326
0.8487	Intermediate Similarity	NPC153700
0.8487	Intermediate Similarity	NPC170538
0.8482	Intermediate Similarity	NPC177064
0.8475	Intermediate Similarity	NPC79579
0.8468	Intermediate Similarity	NPC60681
0.8468	Intermediate Similarity	NPC149047
0.8468	Intermediate Similarity	NPC196528
0.8468	Intermediate Similarity	NPC181265
0.8462	Intermediate Similarity	NPC50774
0.8462	Intermediate Similarity	NPC118638
0.8462	Intermediate Similarity	NPC153440
0.8462	Intermediate Similarity	NPC709
0.8455	Intermediate Similarity	NPC191892
0.8455	Intermediate Similarity	NPC196921
0.8455	Intermediate Similarity	NPC264048
0.8455	Intermediate Similarity	NPC220757
0.8448	Intermediate Similarity	NPC196931
0.8448	Intermediate Similarity	NPC190286
0.8448	Intermediate Similarity	NPC270929
0.8448	Intermediate Similarity	NPC64318
0.8435	Intermediate Similarity	NPC202889
0.8435	Intermediate Similarity	NPC122056
0.843	Intermediate Similarity	NPC293112
0.8417	Intermediate Similarity	NPC469789
0.8407	Intermediate Similarity	NPC284828
0.8407	Intermediate Similarity	NPC241927
0.8407	Intermediate Similarity	NPC472216
0.8407	Intermediate Similarity	NPC41405
0.8407	Intermediate Similarity	NPC475065
0.8407	Intermediate Similarity	NPC11710
0.8407	Intermediate Similarity	NPC258543
0.8407	Intermediate Similarity	NPC173905
0.8407	Intermediate Similarity	NPC5475
0.8407	Intermediate Similarity	NPC304495
0.8403	Intermediate Similarity	NPC310511
0.8403	Intermediate Similarity	NPC46570
0.8393	Intermediate Similarity	NPC477916
0.8393	Intermediate Similarity	NPC144459
0.8393	Intermediate Similarity	NPC165873
0.8393	Intermediate Similarity	NPC255387
0.8393	Intermediate Similarity	NPC220229
0.8393	Intermediate Similarity	NPC475060
0.8393	Intermediate Similarity	NPC131665
0.8393	Intermediate Similarity	NPC83744
0.839	Intermediate Similarity	NPC472933
0.839	Intermediate Similarity	NPC475775
0.839	Intermediate Similarity	NPC476529
0.8387	Intermediate Similarity	NPC34963
0.8378	Intermediate Similarity	NPC137657
0.8378	Intermediate Similarity	NPC235889
0.8378	Intermediate Similarity	NPC118911
0.8378	Intermediate Similarity	NPC204833
0.8378	Intermediate Similarity	NPC209502
0.8376	Intermediate Similarity	NPC183580
0.8376	Intermediate Similarity	NPC472934
0.8376	Intermediate Similarity	NPC470493
0.8376	Intermediate Similarity	NPC243065
0.8376	Intermediate Similarity	NPC312824
0.8374	Intermediate Similarity	NPC470880
0.8374	Intermediate Similarity	NPC221414
0.8364	Intermediate Similarity	NPC114540
0.8364	Intermediate Similarity	NPC473928
0.8364	Intermediate Similarity	NPC32577
0.8364	Intermediate Similarity	NPC155332
0.8364	Intermediate Similarity	NPC136289
0.8364	Intermediate Similarity	NPC185530
0.8364	Intermediate Similarity	NPC473424
0.8362	Intermediate Similarity	NPC178289
0.8361	Intermediate Similarity	NPC473253
0.8349	Intermediate Similarity	NPC144956
0.8349	Intermediate Similarity	NPC316964
0.8348	Intermediate Similarity	NPC191620
0.8348	Intermediate Similarity	NPC207251
0.8348	Intermediate Similarity	NPC170487
0.8347	Intermediate Similarity	NPC8369
0.8347	Intermediate Similarity	NPC8374
0.8347	Intermediate Similarity	NPC3381
0.8333	Intermediate Similarity	NPC239097
0.8333	Intermediate Similarity	NPC107493
0.8333	Intermediate Similarity	NPC257017
0.8333	Intermediate Similarity	NPC23786
0.8333	Intermediate Similarity	NPC470265
0.8333	Intermediate Similarity	NPC197428
0.8333	Intermediate Similarity	NPC162009
0.8333	Intermediate Similarity	NPC76084
0.8333	Intermediate Similarity	NPC5284
0.832	Intermediate Similarity	NPC469673
0.832	Intermediate Similarity	NPC58029
0.8319	Intermediate Similarity	NPC318363
0.8319	Intermediate Similarity	NPC474585
0.8319	Intermediate Similarity	NPC473482
0.8319	Intermediate Similarity	NPC217201
0.8319	Intermediate Similarity	NPC295244
0.8319	Intermediate Similarity	NPC109607
0.8319	Intermediate Similarity	NPC329417
0.8319	Intermediate Similarity	NPC107338
0.8319	Intermediate Similarity	NPC475418
0.8306	Intermediate Similarity	NPC241935
0.8306	Intermediate Similarity	NPC279478
0.8306	Intermediate Similarity	NPC213634
0.8305	Intermediate Similarity	NPC146786
0.8304	Intermediate Similarity	NPC49958
0.8304	Intermediate Similarity	NPC85829
0.8304	Intermediate Similarity	NPC171137
0.8304	Intermediate Similarity	NPC476027
0.8304	Intermediate Similarity	NPC202167
0.8304	Intermediate Similarity	NPC50692
0.8304	Intermediate Similarity	NPC97202
0.8304	Intermediate Similarity	NPC214264
0.8304	Intermediate Similarity	NPC302607
0.8304	Intermediate Similarity	NPC48733
0.8304	Intermediate Similarity	NPC150531
0.8304	Intermediate Similarity	NPC319077
0.8304	Intermediate Similarity	NPC296945
0.8304	Intermediate Similarity	NPC257353
0.8304	Intermediate Similarity	NPC260268
0.8304	Intermediate Similarity	NPC152695
0.8288	Intermediate Similarity	NPC26478
0.8288	Intermediate Similarity	NPC112009
0.8288	Intermediate Similarity	NPC180204
0.8288	Intermediate Similarity	NPC111323
0.8281	Intermediate Similarity	NPC79250
0.8281	Intermediate Similarity	NPC290746
0.8276	Intermediate Similarity	NPC194100
0.8276	Intermediate Similarity	NPC472929
0.8276	Intermediate Similarity	NPC472926
0.8276	Intermediate Similarity	NPC25909
0.8276	Intermediate Similarity	NPC317210
0.8273	Intermediate Similarity	NPC476223
0.8273	Intermediate Similarity	NPC476240
0.8273	Intermediate Similarity	NPC224720
0.8273	Intermediate Similarity	NPC81530
0.8264	Intermediate Similarity	NPC204812
0.8264	Intermediate Similarity	NPC120724
0.8261	Intermediate Similarity	NPC214797

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 NPC257457 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1446
0.2-0.3	3572
0.3-0.4	2544
0.4-0.5	836
0.5-0.6	249
0.6-0.7	131
0.7-0.8	115
0.8-0.85	32
0.85-0.9	25
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9009	High Similarity	NPD8297	Approved
0.8919	High Similarity	NPD6650	Approved
0.8919	High Similarity	NPD6649	Approved
0.8818	High Similarity	NPD6881	Approved
0.8818	High Similarity	NPD6899	Approved
0.875	High Similarity	NPD8130	Phase 1
0.8739	High Similarity	NPD6373	Approved
0.8739	High Similarity	NPD6372	Approved
0.8727	High Similarity	NPD5697	Approved
0.8673	High Similarity	NPD6882	Approved
0.8661	High Similarity	NPD6883	Approved
0.8661	High Similarity	NPD7290	Approved
0.8661	High Similarity	NPD7102	Approved
0.8636	High Similarity	NPD7128	Approved
0.8636	High Similarity	NPD6402	Approved
0.8636	High Similarity	NPD6675	Approved
0.8636	High Similarity	NPD5739	Approved
0.8584	High Similarity	NPD6617	Approved
0.8584	High Similarity	NPD6847	Approved
0.8584	High Similarity	NPD6869	Approved
0.8571	High Similarity	NPD6014	Approved
0.8571	High Similarity	NPD6012	Approved
0.8571	High Similarity	NPD6013	Approved
0.8534	High Similarity	NPD7115	Discovery
0.8482	Intermediate Similarity	NPD6011	Approved
0.8482	Intermediate Similarity	NPD7320	Approved
0.8393	Intermediate Similarity	NPD5701	Approved
0.8364	Intermediate Similarity	NPD5211	Phase 2
0.8349	Intermediate Similarity	NPD5286	Approved
0.8349	Intermediate Similarity	NPD5285	Approved
0.8349	Intermediate Similarity	NPD4696	Approved
0.8319	Intermediate Similarity	NPD6319	Approved
0.8276	Intermediate Similarity	NPD4632	Approved
0.8214	Intermediate Similarity	NPD5141	Approved
0.8198	Intermediate Similarity	NPD5225	Approved
0.8198	Intermediate Similarity	NPD5224	Approved
0.8198	Intermediate Similarity	NPD5226	Approved
0.8198	Intermediate Similarity	NPD4633	Approved
0.8165	Intermediate Similarity	NPD6084	Phase 2
0.8165	Intermediate Similarity	NPD6083	Phase 2
0.8165	Intermediate Similarity	NPD4755	Approved
0.8125	Intermediate Similarity	NPD5174	Approved
0.8125	Intermediate Similarity	NPD5175	Approved
0.8108	Intermediate Similarity	NPD5223	Approved
0.8103	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8083	Intermediate Similarity	NPD7101	Approved
0.8083	Intermediate Similarity	NPD7100	Approved
0.8018	Intermediate Similarity	NPD4700	Approved
0.8017	Intermediate Similarity	NPD4634	Approved
0.8	Intermediate Similarity	NPD6335	Approved
0.8	Intermediate Similarity	NPD4729	Approved
0.8	Intermediate Similarity	NPD4730	Approved
0.7983	Intermediate Similarity	NPD6274	Approved
0.7928	Intermediate Similarity	NPD5696	Approved
0.7917	Intermediate Similarity	NPD6009	Approved
0.7917	Intermediate Similarity	NPD6317	Approved
0.7909	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD5222	Approved
0.7909	Intermediate Similarity	NPD5221	Approved
0.7903	Intermediate Similarity	NPD7492	Approved
0.787	Intermediate Similarity	NPD6079	Approved
0.7869	Intermediate Similarity	NPD6054	Approved
0.7863	Intermediate Similarity	NPD5247	Approved
0.7863	Intermediate Similarity	NPD5248	Approved
0.7863	Intermediate Similarity	NPD5250	Approved
0.7863	Intermediate Similarity	NPD5249	Phase 3
0.7863	Intermediate Similarity	NPD5251	Approved
0.7857	Intermediate Similarity	NPD7736	Approved
0.7851	Intermediate Similarity	NPD6314	Approved
0.7851	Intermediate Similarity	NPD6313	Approved
0.784	Intermediate Similarity	NPD6616	Approved
0.784	Intermediate Similarity	NPD7507	Approved
0.7838	Intermediate Similarity	NPD5173	Approved
0.7826	Intermediate Similarity	NPD4768	Approved
0.7826	Intermediate Similarity	NPD4767	Approved
0.7823	Intermediate Similarity	NPD7604	Phase 2
0.7818	Intermediate Similarity	NPD5695	Phase 3
0.7818	Intermediate Similarity	NPD5210	Approved
0.7818	Intermediate Similarity	NPD4629	Approved
0.7805	Intermediate Similarity	NPD5983	Phase 2
0.7805	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7078	Approved
0.7768	Intermediate Similarity	NPD7638	Approved
0.7748	Intermediate Similarity	NPD4697	Phase 3
0.7742	Intermediate Similarity	NPD6370	Approved
0.7706	Intermediate Similarity	NPD5693	Phase 1
0.7699	Intermediate Similarity	NPD7639	Approved
0.7699	Intermediate Similarity	NPD7640	Approved
0.7698	Intermediate Similarity	NPD6336	Discontinued
0.7692	Intermediate Similarity	NPD5128	Approved
0.7686	Intermediate Similarity	NPD6868	Approved
0.7685	Intermediate Similarity	NPD5328	Approved
0.7685	Intermediate Similarity	NPD4753	Phase 2
0.7672	Intermediate Similarity	NPD6008	Approved
0.7661	Intermediate Similarity	NPD6909	Approved
0.7661	Intermediate Similarity	NPD6016	Approved
0.7661	Intermediate Similarity	NPD6015	Approved
0.7661	Intermediate Similarity	NPD6908	Approved
0.7656	Intermediate Similarity	NPD7319	Approved
0.7652	Intermediate Similarity	NPD4754	Approved
0.7647	Intermediate Similarity	NPD5216	Approved
0.7647	Intermediate Similarity	NPD5215	Approved
0.7647	Intermediate Similarity	NPD5217	Approved
0.7638	Intermediate Similarity	NPD8293	Discontinued
0.7636	Intermediate Similarity	NPD6399	Phase 3
0.7611	Intermediate Similarity	NPD4225	Approved
0.76	Intermediate Similarity	NPD5988	Approved
0.7581	Intermediate Similarity	NPD6059	Approved
0.7563	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD5135	Approved
0.7563	Intermediate Similarity	NPD5169	Approved
0.7542	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6673	Approved
0.7523	Intermediate Similarity	NPD6904	Approved
0.7523	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5127	Approved
0.7477	Intermediate Similarity	NPD4202	Approved
0.7438	Intermediate Similarity	NPD6053	Discontinued
0.7431	Intermediate Similarity	NPD5737	Approved
0.7431	Intermediate Similarity	NPD6672	Approved
0.7411	Intermediate Similarity	NPD7748	Approved
0.7407	Intermediate Similarity	NPD3618	Phase 1
0.7407	Intermediate Similarity	NPD7334	Approved
0.7407	Intermediate Similarity	NPD7146	Approved
0.7407	Intermediate Similarity	NPD5330	Approved
0.7407	Intermediate Similarity	NPD7521	Approved
0.7407	Intermediate Similarity	NPD6409	Approved
0.7407	Intermediate Similarity	NPD6684	Approved
0.7381	Intermediate Similarity	NPD7503	Approved
0.7381	Intermediate Similarity	NPD8033	Approved
0.7368	Intermediate Similarity	NPD7902	Approved
0.736	Intermediate Similarity	NPD7516	Approved
0.7333	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5167	Approved
0.7315	Intermediate Similarity	NPD5329	Approved
0.7302	Intermediate Similarity	NPD8377	Approved
0.7302	Intermediate Similarity	NPD8294	Approved
0.7297	Intermediate Similarity	NPD5785	Approved
0.728	Intermediate Similarity	NPD7327	Approved
0.728	Intermediate Similarity	NPD7328	Approved
0.7273	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6903	Approved
0.7266	Intermediate Similarity	NPD8328	Phase 3
0.725	Intermediate Similarity	NPD5168	Approved
0.725	Intermediate Similarity	NPD6686	Approved
0.7248	Intermediate Similarity	NPD6098	Approved
0.7248	Intermediate Similarity	NPD5690	Phase 2
0.7244	Intermediate Similarity	NPD8380	Approved
0.7244	Intermediate Similarity	NPD8335	Approved
0.7244	Intermediate Similarity	NPD8379	Approved
0.7244	Intermediate Similarity	NPD8378	Approved
0.7244	Intermediate Similarity	NPD8296	Approved
0.7232	Intermediate Similarity	NPD7515	Phase 2
0.7232	Intermediate Similarity	NPD5284	Approved
0.7232	Intermediate Similarity	NPD6050	Approved
0.7232	Intermediate Similarity	NPD5281	Approved
0.7232	Intermediate Similarity	NPD5694	Approved
0.7222	Intermediate Similarity	NPD4197	Approved
0.7222	Intermediate Similarity	NPD3133	Approved
0.7222	Intermediate Similarity	NPD3665	Phase 1
0.7222	Intermediate Similarity	NPD4786	Approved
0.7222	Intermediate Similarity	NPD3666	Approved
0.7183	Intermediate Similarity	NPD7236	Approved
0.7182	Intermediate Similarity	NPD3573	Approved
0.7167	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6412	Phase 2
0.7156	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7143	Intermediate Similarity	NPD7260	Phase 2
0.7119	Intermediate Similarity	NPD7632	Discontinued
0.7105	Intermediate Similarity	NPD7900	Approved
0.7105	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6001	Approved
0.7091	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD8035	Phase 2
0.708	Intermediate Similarity	NPD8034	Phase 2
0.7055	Intermediate Similarity	NPD7239	Suspended
0.7054	Intermediate Similarity	NPD6051	Approved
0.7045	Intermediate Similarity	NPD6033	Approved
0.7037	Intermediate Similarity	NPD3667	Approved
0.7037	Intermediate Similarity	NPD4223	Phase 3
0.7037	Intermediate Similarity	NPD4221	Approved
0.7025	Intermediate Similarity	NPD6614	Approved
0.7025	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6371	Approved
0.6991	Remote Similarity	NPD5207	Approved
0.6977	Remote Similarity	NPD6921	Approved
0.6964	Remote Similarity	NPD5208	Approved
0.696	Remote Similarity	NPD8133	Approved
0.6937	Remote Similarity	NPD5279	Phase 3
0.6937	Remote Similarity	NPD4694	Approved
0.6937	Remote Similarity	NPD5280	Approved
0.693	Remote Similarity	NPD6411	Approved
0.6929	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7520	Clinical (unspecified phase)

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