NPASS Compound

Structure

NPC87351 OpenBabel07101718332D 36 39 0 0 1 0 0 0 0 0999 V2000 -2.9855 -2.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2424 -3.3087 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 -3.4641 1.0000 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 -4.3301 1.5000 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 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 -2.5981 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 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 -4.3301 2.5000 0.0000 C 0 0 0 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 -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 2.5388 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 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 -2.3435 -1.3795 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 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 15 27 1 0 0 0 0 16 23 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 29 1 6 0 0 0 19 24 1 0 0 0 0 19 31 1 1 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 26 1 0 0 0 0 21 32 2 0 0 0 0 22 30 1 0 0 0 0 22 33 2 0 0 0 0 23 29 1 0 0 0 0 23 34 2 0 0 0 0 24 28 1 6 0 0 0 24 30 1 0 0 0 0 25 35 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 6 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.31
Volume:	532.769
LogP:	2.438
LogD:	2.475
LogS:	-4.68
# Rotatable Bonds:	4
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	5.166
Fsp3:	0.767
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:	-4.968
MDCK Permeability:	1.7293223208980635e-05
Pgp-inhibitor:	0.789
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.24
30% Bioavailability (F30%):	0.698

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98
Plasma Protein Binding (PPB):	71.26345825195312%
Volume Distribution (VD):	0.569
Pgp-substrate:	18.886882781982422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.389
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.841
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.698

ADMET: Excretion

Clearance (CL):	4.03
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.756
Maximum Recommended Daily Dose:	0.799
Skin Sensitization:	0.076
Carcinogencity:	0.786
Eye Corrosion:	0.004
Eye Irritation:	0.038
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC87351

Natural Product ID:	NPC87351
*Common Name:**	2-Deoxycucurbitacin D
IUPAC Name:	(8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:	2-Deoxycucurbitacin D
Standard InCHIKey:	KMFVVUWIGLRRLZ-NTLQYXAJSA-N
Standard InCHI:	InChI=1S/C30H44O6/c1-25(2,35)14-13-22(33)30(8,36)24-19(31)15-27(5)20-11-9-17-18(10-12-21(32)26(17,3)4)29(20,7)23(34)16-28(24,27)6/h9,13-14,18-20,24,31,35-36H,10-12,15-16H2,1-8H3/b14-13+/t18-,19-,20+,24+,27+,28-,29+,30+/m1/s1
SMILES:	O[C@@H]1C[C@@]2([C@]([C@H]1[C@](C(=O)/C=C/C(O)(C)C)(O)C)(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1CCC(=O)C2(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL493647
PubChem CID:	21597452
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]
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

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	41.0	nM	PMID[489556]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	32.0	nM	PMID[489556]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	210.0	nM	PMID[489556]

☑ 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 NPC87351 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	189
0.1-0.2	1121
0.2-0.3	4487
0.3-0.4	10337
0.4-0.5	11501
0.5-0.6	7114
0.6-0.7	5680
0.7-0.8	1960
0.8-0.85	216
0.85-0.9	81
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC311612
0.9688	High Similarity	NPC111323
0.9592	High Similarity	NPC185
0.94	High Similarity	NPC214644
0.9158	High Similarity	NPC472932
0.91	High Similarity	NPC257353
0.898	High Similarity	NPC474720
0.898	High Similarity	NPC144956
0.8942	High Similarity	NPC475524
0.8942	High Similarity	NPC100267
0.89	High Similarity	NPC249187
0.89	High Similarity	NPC247957
0.8878	High Similarity	NPC197386
0.8868	High Similarity	NPC148458
0.8866	High Similarity	NPC49371
0.883	High Similarity	NPC326627
0.883	High Similarity	NPC310010
0.883	High Similarity	NPC2983
0.883	High Similarity	NPC477943
0.8812	High Similarity	NPC137657
0.88	High Similarity	NPC473424
0.88	High Similarity	NPC477915
0.8785	High Similarity	NPC471854
0.8776	High Similarity	NPC18509
0.8762	High Similarity	NPC221144
0.875	High Similarity	NPC233118
0.875	High Similarity	NPC472930
0.875	High Similarity	NPC474736
0.8737	High Similarity	NPC320026
0.8725	High Similarity	NPC149047
0.8679	High Similarity	NPC108721
0.8679	High Similarity	NPC73300
0.8673	High Similarity	NPC249954
0.8673	High Similarity	NPC471463
0.866	High Similarity	NPC8993
0.8646	High Similarity	NPC475806
0.8641	High Similarity	NPC475294
0.8641	High Similarity	NPC475060
0.8641	High Similarity	NPC83744
0.8641	High Similarity	NPC477916
0.8641	High Similarity	NPC220229
0.8632	High Similarity	NPC76879
0.8627	High Similarity	NPC235889
0.8627	High Similarity	NPC72255
0.8627	High Similarity	NPC209502
0.8627	High Similarity	NPC204833
0.8614	High Similarity	NPC195290
0.8614	High Similarity	NPC204450
0.8611	High Similarity	NPC239273
0.86	High Similarity	NPC154072
0.8586	High Similarity	NPC107243
0.8571	High Similarity	NPC259286
0.8558	High Similarity	NPC217201
0.8558	High Similarity	NPC329417
0.8558	High Similarity	NPC177064
0.8558	High Similarity	NPC65941
0.8557	High Similarity	NPC474807
0.8557	High Similarity	NPC472942
0.8544	High Similarity	NPC150531
0.8544	High Similarity	NPC60681
0.8544	High Similarity	NPC171137
0.8544	High Similarity	NPC152695
0.8544	High Similarity	NPC260268
0.8544	High Similarity	NPC476027
0.8544	High Similarity	NPC50692
0.8544	High Similarity	NPC48733
0.8544	High Similarity	NPC85829
0.8544	High Similarity	NPC319077
0.8544	High Similarity	NPC97202
0.8544	High Similarity	NPC296945
0.8544	High Similarity	NPC49958
0.8544	High Similarity	NPC302607
0.8544	High Similarity	NPC202167
0.8544	High Similarity	NPC181265
0.8544	High Similarity	NPC214264
0.8542	High Similarity	NPC48010
0.8532	High Similarity	NPC311554
0.8532	High Similarity	NPC257457
0.8529	High Similarity	NPC26478
0.8529	High Similarity	NPC191892
0.8529	High Similarity	NPC236390
0.8515	High Similarity	NPC302537
0.8515	High Similarity	NPC163372
0.8511	High Similarity	NPC469994
0.8511	High Similarity	NPC327115
0.85	High Similarity	NPC235464
0.85	High Similarity	NPC166745
0.85	High Similarity	NPC147954
0.8476	Intermediate Similarity	NPC11710
0.8476	Intermediate Similarity	NPC241927
0.8476	Intermediate Similarity	NPC258543
0.8469	Intermediate Similarity	NPC292793
0.8462	Intermediate Similarity	NPC43285
0.8462	Intermediate Similarity	NPC58370
0.8462	Intermediate Similarity	NPC44063
0.8454	Intermediate Similarity	NPC473998
0.8454	Intermediate Similarity	NPC472978
0.8454	Intermediate Similarity	NPC168027
0.8454	Intermediate Similarity	NPC185936
0.8438	Intermediate Similarity	NPC309603
0.8438	Intermediate Similarity	NPC474245
0.8438	Intermediate Similarity	NPC473999
0.8438	Intermediate Similarity	NPC1015
0.8438	Intermediate Similarity	NPC31985
0.8438	Intermediate Similarity	NPC123912
0.8431	Intermediate Similarity	NPC119601
0.8431	Intermediate Similarity	NPC308726
0.8431	Intermediate Similarity	NPC185530
0.8421	Intermediate Similarity	NPC58063
0.8421	Intermediate Similarity	NPC317590
0.8416	Intermediate Similarity	NPC287833
0.8404	Intermediate Similarity	NPC469948
0.8404	Intermediate Similarity	NPC474218
0.8404	Intermediate Similarity	NPC471224
0.84	Intermediate Similarity	NPC57416
0.8384	Intermediate Similarity	NPC318282
0.8384	Intermediate Similarity	NPC180950
0.8384	Intermediate Similarity	NPC173875
0.8384	Intermediate Similarity	NPC469995
0.8384	Intermediate Similarity	NPC271195
0.8384	Intermediate Similarity	NPC174948
0.8381	Intermediate Similarity	NPC295244
0.8367	Intermediate Similarity	NPC69454
0.8367	Intermediate Similarity	NPC125180
0.8351	Intermediate Similarity	NPC171441
0.8351	Intermediate Similarity	NPC69622
0.835	Intermediate Similarity	NPC117185
0.8333	Intermediate Similarity	NPC224720
0.8333	Intermediate Similarity	NPC476240
0.8333	Intermediate Similarity	NPC476223
0.8318	Intermediate Similarity	NPC118860
0.8318	Intermediate Similarity	NPC43775
0.8318	Intermediate Similarity	NPC214797
0.8318	Intermediate Similarity	NPC231589
0.8317	Intermediate Similarity	NPC10364
0.8317	Intermediate Similarity	NPC103051
0.8316	Intermediate Similarity	NPC145879
0.8316	Intermediate Similarity	NPC94666
0.8316	Intermediate Similarity	NPC20688
0.8316	Intermediate Similarity	NPC31564
0.8316	Intermediate Similarity	NPC51014
0.8316	Intermediate Similarity	NPC474733
0.8316	Intermediate Similarity	NPC474732
0.8316	Intermediate Similarity	NPC474778
0.8302	Intermediate Similarity	NPC2766
0.8302	Intermediate Similarity	NPC470257
0.8302	Intermediate Similarity	NPC304495
0.83	Intermediate Similarity	NPC328371
0.83	Intermediate Similarity	NPC192428
0.8298	Intermediate Similarity	NPC476412
0.8298	Intermediate Similarity	NPC214043
0.8298	Intermediate Similarity	NPC237712
0.8298	Intermediate Similarity	NPC321187
0.8298	Intermediate Similarity	NPC58841
0.8298	Intermediate Similarity	NPC161423
0.8298	Intermediate Similarity	NPC227064
0.8298	Intermediate Similarity	NPC85774
0.8298	Intermediate Similarity	NPC144258
0.8298	Intermediate Similarity	NPC329043
0.8298	Intermediate Similarity	NPC82902
0.8286	Intermediate Similarity	NPC165873
0.8286	Intermediate Similarity	NPC472925
0.8283	Intermediate Similarity	NPC299100
0.8283	Intermediate Similarity	NPC473162
0.8283	Intermediate Similarity	NPC196485
0.8283	Intermediate Similarity	NPC472976
0.8283	Intermediate Similarity	NPC473172
0.8283	Intermediate Similarity	NPC245972
0.8283	Intermediate Similarity	NPC472977
0.8283	Intermediate Similarity	NPC474690
0.8269	Intermediate Similarity	NPC149124
0.8269	Intermediate Similarity	NPC75531
0.8265	Intermediate Similarity	NPC63748
0.8252	Intermediate Similarity	NPC136289
0.8247	Intermediate Similarity	NPC472973
0.8247	Intermediate Similarity	NPC472475
0.8247	Intermediate Similarity	NPC472477
0.8247	Intermediate Similarity	NPC186688
0.8247	Intermediate Similarity	NPC262043
0.8241	Intermediate Similarity	NPC170487
0.8241	Intermediate Similarity	NPC71348
0.8241	Intermediate Similarity	NPC207251
0.8235	Intermediate Similarity	NPC15390
0.8235	Intermediate Similarity	NPC205899
0.8235	Intermediate Similarity	NPC51370
0.8235	Intermediate Similarity	NPC218383
0.8235	Intermediate Similarity	NPC476274
0.8235	Intermediate Similarity	NPC83709
0.8229	Intermediate Similarity	NPC90652
0.8229	Intermediate Similarity	NPC475740
0.8229	Intermediate Similarity	NPC93778
0.8224	Intermediate Similarity	NPC37116
0.8224	Intermediate Similarity	NPC76084
0.8224	Intermediate Similarity	NPC235077
0.8218	Intermediate Similarity	NPC18319
0.8218	Intermediate Similarity	NPC474938
0.8218	Intermediate Similarity	NPC126815
0.8218	Intermediate Similarity	NPC474785
0.8218	Intermediate Similarity	NPC475894
0.8211	Intermediate Similarity	NPC476426

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 NPC87351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1374
0.2-0.3	3854
0.3-0.4	2565
0.4-0.5	693
0.5-0.6	173
0.6-0.7	145
0.7-0.8	101
0.8-0.85	58
0.85-0.9	20
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9184	High Similarity	NPD5211	Phase 2
0.9	High Similarity	NPD5141	Approved
0.898	High Similarity	NPD5286	Approved
0.898	High Similarity	NPD5285	Approved
0.898	High Similarity	NPD4696	Approved
0.8958	High Similarity	NPD5210	Approved
0.8958	High Similarity	NPD4629	Approved
0.883	High Similarity	NPD4753	Phase 2
0.88	High Similarity	NPD4633	Approved
0.88	High Similarity	NPD5225	Approved
0.88	High Similarity	NPD5224	Approved
0.88	High Similarity	NPD5226	Approved
0.8776	High Similarity	NPD4755	Approved
0.8713	High Similarity	NPD5175	Approved
0.8713	High Similarity	NPD5174	Approved
0.87	High Similarity	NPD5223	Approved
0.86	High Similarity	NPD4700	Approved
0.8558	High Similarity	NPD6899	Approved
0.8558	High Similarity	NPD6881	Approved
0.8491	Intermediate Similarity	NPD6649	Approved
0.8491	Intermediate Similarity	NPD6650	Approved
0.8485	Intermediate Similarity	NPD5222	Approved
0.8485	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD5221	Approved
0.8462	Intermediate Similarity	NPD5697	Approved
0.8454	Intermediate Similarity	NPD6079	Approved
0.8404	Intermediate Similarity	NPD5329	Approved
0.84	Intermediate Similarity	NPD6084	Phase 2
0.84	Intermediate Similarity	NPD6083	Phase 2
0.84	Intermediate Similarity	NPD5173	Approved
0.8396	Intermediate Similarity	NPD6883	Approved
0.8396	Intermediate Similarity	NPD7290	Approved
0.8396	Intermediate Similarity	NPD7102	Approved
0.8381	Intermediate Similarity	NPD4730	Approved
0.8381	Intermediate Similarity	NPD4729	Approved
0.8365	Intermediate Similarity	NPD5739	Approved
0.8365	Intermediate Similarity	NPD7128	Approved
0.8365	Intermediate Similarity	NPD6675	Approved
0.8365	Intermediate Similarity	NPD6402	Approved
0.8318	Intermediate Similarity	NPD8130	Phase 1
0.8318	Intermediate Similarity	NPD6869	Approved
0.8318	Intermediate Similarity	NPD6617	Approved
0.8318	Intermediate Similarity	NPD6847	Approved
0.8316	Intermediate Similarity	NPD5690	Phase 2
0.8302	Intermediate Similarity	NPD6013	Approved
0.8302	Intermediate Similarity	NPD6012	Approved
0.8302	Intermediate Similarity	NPD6014	Approved
0.8302	Intermediate Similarity	NPD6372	Approved
0.8302	Intermediate Similarity	NPD6373	Approved
0.83	Intermediate Similarity	NPD4697	Phase 3
0.8298	Intermediate Similarity	NPD3133	Approved
0.8298	Intermediate Similarity	NPD4197	Approved
0.8298	Intermediate Similarity	NPD3665	Phase 1
0.8298	Intermediate Similarity	NPD3666	Approved
0.8247	Intermediate Similarity	NPD5328	Approved
0.8241	Intermediate Similarity	NPD8297	Approved
0.8241	Intermediate Similarity	NPD6882	Approved
0.8224	Intermediate Similarity	NPD4634	Approved
0.8224	Intermediate Similarity	NPD5249	Phase 3
0.8224	Intermediate Similarity	NPD5248	Approved
0.8224	Intermediate Similarity	NPD5251	Approved
0.8224	Intermediate Similarity	NPD5250	Approved
0.8224	Intermediate Similarity	NPD5247	Approved
0.8208	Intermediate Similarity	NPD6011	Approved
0.8208	Intermediate Similarity	NPD7320	Approved
0.8208	Intermediate Similarity	NPD5128	Approved
0.819	Intermediate Similarity	NPD4767	Approved
0.819	Intermediate Similarity	NPD4768	Approved
0.8173	Intermediate Similarity	NPD4754	Approved
0.8148	Intermediate Similarity	NPD5217	Approved
0.8148	Intermediate Similarity	NPD5216	Approved
0.8148	Intermediate Similarity	NPD5215	Approved
0.8137	Intermediate Similarity	NPD5696	Approved
0.8113	Intermediate Similarity	NPD5701	Approved
0.8105	Intermediate Similarity	NPD4786	Approved
0.8085	Intermediate Similarity	NPD4223	Phase 3
0.8085	Intermediate Similarity	NPD4221	Approved
0.8056	Intermediate Similarity	NPD5169	Approved
0.8056	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD5135	Approved
0.802	Intermediate Similarity	NPD5695	Phase 3
0.8	Intermediate Similarity	NPD4202	Approved
0.7982	Intermediate Similarity	NPD5127	Approved
0.7938	Intermediate Similarity	NPD4694	Approved
0.7938	Intermediate Similarity	NPD5280	Approved
0.7938	Intermediate Similarity	NPD3618	Phase 1
0.7938	Intermediate Similarity	NPD5279	Phase 3
0.7895	Intermediate Similarity	NPD3667	Approved
0.7838	Intermediate Similarity	NPD4632	Approved
0.7818	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4788	Approved
0.7807	Intermediate Similarity	NPD7100	Approved
0.7807	Intermediate Similarity	NPD7101	Approved
0.7788	Intermediate Similarity	NPD7115	Discovery
0.7768	Intermediate Similarity	NPD5167	Approved
0.7766	Intermediate Similarity	NPD4195	Approved
0.7755	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD4688	Approved
0.7755	Intermediate Similarity	NPD4690	Approved
0.7755	Intermediate Similarity	NPD5205	Approved
0.7755	Intermediate Similarity	NPD4693	Phase 3
0.7755	Intermediate Similarity	NPD4138	Approved
0.7755	Intermediate Similarity	NPD4689	Approved
0.7739	Intermediate Similarity	NPD6054	Approved
0.7736	Intermediate Similarity	NPD5091	Approved
0.7723	Intermediate Similarity	NPD5284	Approved
0.7723	Intermediate Similarity	NPD5281	Approved
0.7719	Intermediate Similarity	NPD6335	Approved
0.7706	Intermediate Similarity	NPD5168	Approved
0.77	Intermediate Similarity	NPD6904	Approved
0.77	Intermediate Similarity	NPD6080	Approved
0.77	Intermediate Similarity	NPD6673	Approved
0.7699	Intermediate Similarity	NPD6274	Approved
0.7684	Intermediate Similarity	NPD4695	Discontinued
0.7647	Intermediate Similarity	NPD6399	Phase 3
0.7632	Intermediate Similarity	NPD6317	Approved
0.7632	Intermediate Similarity	NPD6009	Approved
0.7607	Intermediate Similarity	NPD6370	Approved
0.76	Intermediate Similarity	NPD6672	Approved
0.76	Intermediate Similarity	NPD5737	Approved
0.7586	Intermediate Similarity	NPD6319	Approved
0.7576	Intermediate Similarity	NPD4623	Approved
0.7576	Intermediate Similarity	NPD7146	Approved
0.7576	Intermediate Similarity	NPD4519	Discontinued
0.7576	Intermediate Similarity	NPD7334	Approved
0.7576	Intermediate Similarity	NPD5330	Approved
0.7576	Intermediate Similarity	NPD7521	Approved
0.7576	Intermediate Similarity	NPD6409	Approved
0.7576	Intermediate Similarity	NPD6684	Approved
0.7565	Intermediate Similarity	NPD6313	Approved
0.7565	Intermediate Similarity	NPD6314	Approved
0.7549	Intermediate Similarity	NPD5693	Phase 1
0.7521	Intermediate Similarity	NPD6016	Approved
0.7521	Intermediate Similarity	NPD6015	Approved
0.7521	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD7492	Approved
0.7475	Intermediate Similarity	NPD5363	Approved
0.7474	Intermediate Similarity	NPD3617	Approved
0.7458	Intermediate Similarity	NPD5988	Approved
0.7451	Intermediate Similarity	NPD5785	Approved
0.7436	Intermediate Similarity	NPD6059	Approved
0.7426	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6903	Approved
0.7417	Intermediate Similarity	NPD6616	Approved
0.74	Intermediate Similarity	NPD6098	Approved
0.7395	Intermediate Similarity	NPD7604	Phase 2
0.7391	Intermediate Similarity	NPD6868	Approved
0.7379	Intermediate Similarity	NPD6050	Approved
0.7379	Intermediate Similarity	NPD5694	Approved
0.7374	Intermediate Similarity	NPD3668	Phase 3
0.7373	Intermediate Similarity	NPD6908	Approved
0.7373	Intermediate Similarity	NPD6909	Approved
0.7373	Intermediate Similarity	NPD5983	Phase 2
0.7364	Intermediate Similarity	NPD6008	Approved
0.7355	Intermediate Similarity	NPD7078	Approved
0.735	Intermediate Similarity	NPD4522	Approved
0.7333	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5133	Approved
0.7297	Intermediate Similarity	NPD6412	Phase 2
0.7295	Intermediate Similarity	NPD7736	Approved
0.7282	Intermediate Similarity	NPD5692	Phase 3
0.7281	Intermediate Similarity	NPD6053	Discontinued
0.7273	Intermediate Similarity	NPD6336	Discontinued
0.7263	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4518	Approved
0.7234	Intermediate Similarity	NPD4784	Approved
0.7234	Intermediate Similarity	NPD4785	Approved
0.7228	Intermediate Similarity	NPD5786	Approved
0.7222	Intermediate Similarity	NPD7639	Approved
0.7222	Intermediate Similarity	NPD7640	Approved
0.7212	Intermediate Similarity	NPD7515	Phase 2
0.7172	Intermediate Similarity	NPD4270	Approved
0.7172	Intermediate Similarity	NPD4269	Approved
0.7158	Intermediate Similarity	NPD7339	Approved
0.7158	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD6614	Approved
0.713	Intermediate Similarity	NPD7638	Approved
0.7129	Intermediate Similarity	NPD1696	Phase 3
0.7115	Intermediate Similarity	NPD4096	Approved
0.7115	Intermediate Similarity	NPD5207	Approved
0.7113	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5362	Discontinued
0.7087	Intermediate Similarity	NPD5208	Approved
0.7073	Intermediate Similarity	NPD8293	Discontinued
0.7071	Intermediate Similarity	NPD4139	Approved
0.7071	Intermediate Similarity	NPD4692	Approved
0.7021	Intermediate Similarity	NPD4243	Approved
0.7019	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4822	Approved
0.697	Remote Similarity	NPD4819	Approved
0.697	Remote Similarity	NPD4820	Approved
0.697	Remote Similarity	NPD7514	Phase 3
0.697	Remote Similarity	NPD4821	Approved
0.697	Remote Similarity	NPD6930	Phase 2
0.697	Remote Similarity	NPD4252	Approved
0.697	Remote Similarity	NPD5368	Approved
0.697	Remote Similarity	NPD7525	Registered
0.697	Remote Similarity	NPD6931	Approved
0.6931	Remote Similarity	NPD6695	Phase 3

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