NPASS Compound

Structure

NPC474720 OpenBabel07101718202D 37 40 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 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 2.5981 -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 3 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 -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 3 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 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 1 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 2.3435 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 10 1 0 0 0 0 9 16 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 18 2 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 22 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 0 0 0 0 18 24 1 0 0 0 0 18 31 1 0 0 0 0 19 23 1 0 0 0 0 19 32 1 1 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 21 33 2 0 0 0 0 22 29 1 0 0 0 0 22 34 2 0 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 35 2 0 0 0 0 25 36 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 1 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.31
Volume:	541.559
LogP:	2.236
LogD:	1.901
LogS:	-4.266
# Rotatable Bonds:	5
TPSA:	128.97
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	5.547
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.184
MDCK Permeability:	2.4848075554473326e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.132
Human Intestinal Absorption (HIA):	0.118
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973
Plasma Protein Binding (PPB):	73.55014038085938%
Volume Distribution (VD):	0.42
Pgp-substrate:	20.969078063964844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.715
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.69

ADMET: Excretion

Clearance (CL):	7.633
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.201
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.529
Skin Sensitization:	0.15
Carcinogencity:	0.782
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC474720

Natural Product ID:	NPC474720
*Common Name:**	Cucurbitacin L
IUPAC Name:	(8S,9R,13R,14S,16R)-17-[(2S)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:	Cucurbitacin L
Standard InCHIKey:	PIGAXYFCLPQWOD-CBJCAJNSSA-N
Standard InCHI:	InChI=1S/C30H44O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,13,17,19-20,23,31-32,36-37H,10-12,14-15H2,1-8H3/t17?,19-,20+,23?,27+,28-,29+,30-/m1/s1
SMILES:	OC1=CC2C(=CC[C@@H]3[C@@]2(C)C(=O)C[C@]2([C@@]3(C)C[C@H](C2[C@@](C(=O)CCC(O)(C)C)(O)C)O)C)C(C1=O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480111
PubChem CID:	44559734
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
NPO32650	conobea scoparioides	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7852999]

☑ 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	4

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4306	Cell Line	JY	Homo sapiens	Inhibition	=	69.0	%	PMID[538240]
NPT2536	Individual Protein	Leukocyte adhesion glycoprotein LFA-1 alpha	Homo sapiens	IC50	>	50000.0	nM	PMID[538240]
NPT2	Others	Unspecified		Inhibition	=	77.7	%	PMID[538240]
NPT2	Others	Unspecified		Inhibition	=	79.2	%	PMID[538240]
NPT2	Others	Unspecified		Inhibition	=	86.2	%	PMID[538240]

☑ 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 NPC474720 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	184
0.1-0.2	1294
0.2-0.3	5443
0.3-0.4	11857
0.4-0.5	9857
0.5-0.6	7114
0.6-0.7	5363
0.7-0.8	1357
0.8-0.85	200
0.85-0.9	19
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC43285
0.9388	High Similarity	NPC58370
0.9278	High Similarity	NPC111323
0.9255	High Similarity	NPC49371
0.92	High Similarity	NPC470257
0.92	High Similarity	NPC304495
0.9062	High Similarity	NPC147954
0.898	High Similarity	NPC87351
0.8889	High Similarity	NPC311612
0.8817	High Similarity	NPC326627
0.8817	High Similarity	NPC477943
0.8817	High Similarity	NPC310010
0.8776	High Similarity	NPC144956
0.8763	High Similarity	NPC18509
0.875	High Similarity	NPC472932
0.8737	High Similarity	NPC233118
0.87	High Similarity	NPC191892
0.87	High Similarity	NPC117185
0.8627	High Similarity	NPC185
0.8614	High Similarity	NPC137657
0.8571	High Similarity	NPC221144
0.8544	High Similarity	NPC65941
0.8542	High Similarity	NPC206810
0.8542	High Similarity	NPC472930
0.8529	High Similarity	NPC196528
0.8529	High Similarity	NPC257353
0.8495	Intermediate Similarity	NPC327115
0.8485	Intermediate Similarity	NPC197386
0.8478	Intermediate Similarity	NPC473246
0.8462	Intermediate Similarity	NPC241927
0.8462	Intermediate Similarity	NPC258543
0.8462	Intermediate Similarity	NPC214644
0.8454	Intermediate Similarity	NPC245972
0.8454	Intermediate Similarity	NPC111015
0.8454	Intermediate Similarity	NPC196485
0.8447	Intermediate Similarity	NPC83744
0.8447	Intermediate Similarity	NPC165873
0.8447	Intermediate Similarity	NPC477916
0.8438	Intermediate Similarity	NPC168027
0.8438	Intermediate Similarity	NPC185936
0.8431	Intermediate Similarity	NPC204833
0.8431	Intermediate Similarity	NPC209502
0.8421	Intermediate Similarity	NPC76879
0.8421	Intermediate Similarity	NPC275740
0.8421	Intermediate Similarity	NPC86319
0.8421	Intermediate Similarity	NPC186688
0.8416	Intermediate Similarity	NPC473424
0.84	Intermediate Similarity	NPC83709
0.84	Intermediate Similarity	NPC15390
0.84	Intermediate Similarity	NPC154072
0.8387	Intermediate Similarity	NPC474218
0.8381	Intermediate Similarity	NPC235077
0.8365	Intermediate Similarity	NPC329417
0.8351	Intermediate Similarity	NPC25750
0.8351	Intermediate Similarity	NPC250575
0.8351	Intermediate Similarity	NPC474807
0.835	Intermediate Similarity	NPC48733
0.835	Intermediate Similarity	NPC296945
0.835	Intermediate Similarity	NPC97202
0.835	Intermediate Similarity	NPC85829
0.835	Intermediate Similarity	NPC49958
0.835	Intermediate Similarity	NPC260268
0.835	Intermediate Similarity	NPC50692
0.835	Intermediate Similarity	NPC149047
0.835	Intermediate Similarity	NPC202167
0.835	Intermediate Similarity	NPC319077
0.835	Intermediate Similarity	NPC476027
0.835	Intermediate Similarity	NPC152695
0.835	Intermediate Similarity	NPC171137
0.835	Intermediate Similarity	NPC214264
0.835	Intermediate Similarity	NPC302607
0.835	Intermediate Similarity	NPC150531
0.8333	Intermediate Similarity	NPC129913
0.8333	Intermediate Similarity	NPC148458
0.8333	Intermediate Similarity	NPC171441
0.8333	Intermediate Similarity	NPC249187
0.8333	Intermediate Similarity	NPC247957
0.8318	Intermediate Similarity	NPC108721
0.8318	Intermediate Similarity	NPC73300
0.8317	Intermediate Similarity	NPC472924
0.8316	Intermediate Similarity	NPC131470
0.8316	Intermediate Similarity	NPC143767
0.8302	Intermediate Similarity	NPC43775
0.8302	Intermediate Similarity	NPC214797
0.8302	Intermediate Similarity	NPC118860
0.8302	Intermediate Similarity	NPC231589
0.8288	Intermediate Similarity	NPC42675
0.8283	Intermediate Similarity	NPC249954
0.8283	Intermediate Similarity	NPC305483
0.8283	Intermediate Similarity	NPC192428
0.8283	Intermediate Similarity	NPC173272
0.8283	Intermediate Similarity	NPC96859
0.8283	Intermediate Similarity	NPC328162
0.828	Intermediate Similarity	NPC82902
0.828	Intermediate Similarity	NPC237712
0.828	Intermediate Similarity	NPC144258
0.828	Intermediate Similarity	NPC227064
0.828	Intermediate Similarity	NPC321187
0.828	Intermediate Similarity	NPC85774
0.828	Intermediate Similarity	NPC58841
0.828	Intermediate Similarity	NPC161423
0.828	Intermediate Similarity	NPC214043
0.828	Intermediate Similarity	NPC329043
0.8269	Intermediate Similarity	NPC44063
0.8269	Intermediate Similarity	NPC472925
0.8269	Intermediate Similarity	NPC220229
0.8269	Intermediate Similarity	NPC475060
0.8261	Intermediate Similarity	NPC103486
0.8257	Intermediate Similarity	NPC239273
0.8252	Intermediate Similarity	NPC72255
0.8252	Intermediate Similarity	NPC235889
0.8247	Intermediate Similarity	NPC19114
0.8235	Intermediate Similarity	NPC195290
0.8235	Intermediate Similarity	NPC477915
0.8235	Intermediate Similarity	NPC204450
0.8229	Intermediate Similarity	NPC31985
0.8229	Intermediate Similarity	NPC123912
0.8229	Intermediate Similarity	NPC1015
0.8229	Intermediate Similarity	NPC474245
0.8229	Intermediate Similarity	NPC54689
0.8224	Intermediate Similarity	NPC100267
0.8224	Intermediate Similarity	NPC475524
0.8224	Intermediate Similarity	NPC170487
0.8224	Intermediate Similarity	NPC71348
0.8218	Intermediate Similarity	NPC287833
0.8218	Intermediate Similarity	NPC218383
0.8211	Intermediate Similarity	NPC136548
0.8211	Intermediate Similarity	NPC90652
0.8211	Intermediate Similarity	NPC317590
0.82	Intermediate Similarity	NPC477267
0.82	Intermediate Similarity	NPC190554
0.82	Intermediate Similarity	NPC43747
0.82	Intermediate Similarity	NPC472690
0.82	Intermediate Similarity	NPC477268
0.82	Intermediate Similarity	NPC472689
0.8191	Intermediate Similarity	NPC469948
0.819	Intermediate Similarity	NPC217201
0.8182	Intermediate Similarity	NPC259286
0.8182	Intermediate Similarity	NPC241156
0.8182	Intermediate Similarity	NPC472824
0.8182	Intermediate Similarity	NPC200702
0.8182	Intermediate Similarity	NPC127063
0.8182	Intermediate Similarity	NPC271195
0.8182	Intermediate Similarity	NPC48330
0.8173	Intermediate Similarity	NPC181265
0.8163	Intermediate Similarity	NPC69454
0.8163	Intermediate Similarity	NPC66429
0.8163	Intermediate Similarity	NPC472942
0.8163	Intermediate Similarity	NPC243866
0.8163	Intermediate Similarity	NPC152897
0.8155	Intermediate Similarity	NPC236390
0.8144	Intermediate Similarity	NPC289213
0.8144	Intermediate Similarity	NPC320026
0.8144	Intermediate Similarity	NPC191684
0.8144	Intermediate Similarity	NPC183283
0.8142	Intermediate Similarity	NPC238005
0.8142	Intermediate Similarity	NPC1980
0.8142	Intermediate Similarity	NPC141196
0.8137	Intermediate Similarity	NPC302537
0.8137	Intermediate Similarity	NPC163372
0.8131	Intermediate Similarity	NPC472928
0.8131	Intermediate Similarity	NPC207689
0.8125	Intermediate Similarity	NPC44181
0.8125	Intermediate Similarity	NPC470417
0.8125	Intermediate Similarity	NPC328539
0.8125	Intermediate Similarity	NPC471941
0.8125	Intermediate Similarity	NPC471722
0.8119	Intermediate Similarity	NPC166745
0.8119	Intermediate Similarity	NPC191565
0.8119	Intermediate Similarity	NPC114274
0.8119	Intermediate Similarity	NPC235464
0.8113	Intermediate Similarity	NPC2766
0.8113	Intermediate Similarity	NPC11710
0.8105	Intermediate Similarity	NPC118648
0.8105	Intermediate Similarity	NPC72133
0.8105	Intermediate Similarity	NPC475022
0.8105	Intermediate Similarity	NPC469994
0.8105	Intermediate Similarity	NPC51014
0.8105	Intermediate Similarity	NPC474733
0.8105	Intermediate Similarity	NPC31564
0.8105	Intermediate Similarity	NPC222613
0.8105	Intermediate Similarity	NPC145879
0.8105	Intermediate Similarity	NPC474778
0.8105	Intermediate Similarity	NPC20688
0.8105	Intermediate Similarity	NPC474732
0.81	Intermediate Similarity	NPC155676
0.81	Intermediate Similarity	NPC125622
0.81	Intermediate Similarity	NPC95565
0.81	Intermediate Similarity	NPC42042
0.8081	Intermediate Similarity	NPC473172
0.8081	Intermediate Similarity	NPC103527
0.8081	Intermediate Similarity	NPC166906
0.8077	Intermediate Similarity	NPC255309
0.8065	Intermediate Similarity	NPC193347
0.8061	Intermediate Similarity	NPC154101
0.8061	Intermediate Similarity	NPC63748
0.8061	Intermediate Similarity	NPC131872
0.8061	Intermediate Similarity	NPC233116
0.8058	Intermediate Similarity	NPC22388
0.8058	Intermediate Similarity	NPC293753

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 NPC474720 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1673
0.2-0.3	4200
0.3-0.4	2121
0.4-0.5	541
0.5-0.6	163
0.6-0.7	126
0.7-0.8	106
0.8-0.85	50
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8817	High Similarity	NPD4753	Phase 2
0.8776	High Similarity	NPD4696	Approved
0.8776	High Similarity	NPD5286	Approved
0.8776	High Similarity	NPD5285	Approved
0.8763	High Similarity	NPD4755	Approved
0.875	High Similarity	NPD4629	Approved
0.875	High Similarity	NPD5210	Approved
0.86	High Similarity	NPD4633	Approved
0.86	High Similarity	NPD5225	Approved
0.86	High Similarity	NPD5224	Approved
0.86	High Similarity	NPD5226	Approved
0.86	High Similarity	NPD5211	Phase 2
0.8586	High Similarity	NPD4700	Approved
0.8515	High Similarity	NPD5174	Approved
0.8515	High Similarity	NPD5175	Approved
0.85	High Similarity	NPD5223	Approved
0.8495	Intermediate Similarity	NPD5690	Phase 2
0.8431	Intermediate Similarity	NPD5141	Approved
0.8387	Intermediate Similarity	NPD5329	Approved
0.8384	Intermediate Similarity	NPD6083	Phase 2
0.8384	Intermediate Similarity	NPD6084	Phase 2
0.8381	Intermediate Similarity	NPD4634	Approved
0.8367	Intermediate Similarity	NPD5695	Phase 3
0.8365	Intermediate Similarity	NPD6899	Approved
0.8365	Intermediate Similarity	NPD6881	Approved
0.835	Intermediate Similarity	NPD6675	Approved
0.835	Intermediate Similarity	NPD5739	Approved
0.835	Intermediate Similarity	NPD7128	Approved
0.835	Intermediate Similarity	NPD6402	Approved
0.8302	Intermediate Similarity	NPD6650	Approved
0.8302	Intermediate Similarity	NPD6649	Approved
0.8298	Intermediate Similarity	NPD4694	Approved
0.8298	Intermediate Similarity	NPD5279	Phase 3
0.8298	Intermediate Similarity	NPD5280	Approved
0.8286	Intermediate Similarity	NPD6372	Approved
0.8286	Intermediate Similarity	NPD6373	Approved
0.8283	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8283	Intermediate Similarity	NPD5222	Approved
0.8283	Intermediate Similarity	NPD4697	Phase 3
0.8283	Intermediate Similarity	NPD5221	Approved
0.828	Intermediate Similarity	NPD3665	Phase 1
0.828	Intermediate Similarity	NPD3133	Approved
0.828	Intermediate Similarity	NPD3666	Approved
0.828	Intermediate Similarity	NPD4197	Approved
0.8269	Intermediate Similarity	NPD5697	Approved
0.8247	Intermediate Similarity	NPD6079	Approved
0.8229	Intermediate Similarity	NPD5328	Approved
0.8208	Intermediate Similarity	NPD7290	Approved
0.8208	Intermediate Similarity	NPD7102	Approved
0.8208	Intermediate Similarity	NPD6883	Approved
0.82	Intermediate Similarity	NPD5173	Approved
0.819	Intermediate Similarity	NPD4730	Approved
0.819	Intermediate Similarity	NPD4729	Approved
0.819	Intermediate Similarity	NPD7320	Approved
0.819	Intermediate Similarity	NPD5128	Approved
0.8173	Intermediate Similarity	NPD4768	Approved
0.8173	Intermediate Similarity	NPD4767	Approved
0.8155	Intermediate Similarity	NPD4754	Approved
0.8131	Intermediate Similarity	NPD6869	Approved
0.8131	Intermediate Similarity	NPD8130	Phase 1
0.8131	Intermediate Similarity	NPD6847	Approved
0.8131	Intermediate Similarity	NPD6617	Approved
0.8119	Intermediate Similarity	NPD5696	Approved
0.8113	Intermediate Similarity	NPD6013	Approved
0.8113	Intermediate Similarity	NPD6012	Approved
0.8113	Intermediate Similarity	NPD6014	Approved
0.8095	Intermediate Similarity	NPD5701	Approved
0.8065	Intermediate Similarity	NPD4221	Approved
0.8065	Intermediate Similarity	NPD4223	Phase 3
0.8056	Intermediate Similarity	NPD8297	Approved
0.8056	Intermediate Similarity	NPD6882	Approved
0.8037	Intermediate Similarity	NPD5247	Approved
0.8037	Intermediate Similarity	NPD5249	Phase 3
0.8037	Intermediate Similarity	NPD5251	Approved
0.8037	Intermediate Similarity	NPD5248	Approved
0.8037	Intermediate Similarity	NPD5250	Approved
0.8019	Intermediate Similarity	NPD6011	Approved
0.7982	Intermediate Similarity	NPD4632	Approved
0.798	Intermediate Similarity	NPD4202	Approved
0.7979	Intermediate Similarity	NPD4788	Approved
0.7963	Intermediate Similarity	NPD5216	Approved
0.7963	Intermediate Similarity	NPD5215	Approved
0.7963	Intermediate Similarity	NPD5217	Approved
0.7917	Intermediate Similarity	NPD3618	Phase 1
0.7895	Intermediate Similarity	NPD4786	Approved
0.7879	Intermediate Similarity	NPD5281	Approved
0.7879	Intermediate Similarity	NPD5284	Approved
0.7876	Intermediate Similarity	NPD6054	Approved
0.787	Intermediate Similarity	NPD5135	Approved
0.787	Intermediate Similarity	NPD5169	Approved
0.787	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD5127	Approved
0.7768	Intermediate Similarity	NPD6009	Approved
0.7739	Intermediate Similarity	NPD6370	Approved
0.7732	Intermediate Similarity	NPD4693	Phase 3
0.7732	Intermediate Similarity	NPD4689	Approved
0.7732	Intermediate Similarity	NPD4138	Approved
0.7732	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD4690	Approved
0.7732	Intermediate Similarity	NPD5205	Approved
0.7732	Intermediate Similarity	NPD4688	Approved
0.7719	Intermediate Similarity	NPD6059	Approved
0.7719	Intermediate Similarity	NPD6319	Approved
0.77	Intermediate Similarity	NPD6050	Approved
0.7684	Intermediate Similarity	NPD3667	Approved
0.7679	Intermediate Similarity	NPD6274	Approved
0.7677	Intermediate Similarity	NPD6080	Approved
0.7677	Intermediate Similarity	NPD6904	Approved
0.7677	Intermediate Similarity	NPD6673	Approved
0.766	Intermediate Similarity	NPD4695	Discontinued
0.7652	Intermediate Similarity	NPD6016	Approved
0.7652	Intermediate Similarity	NPD6015	Approved
0.7634	Intermediate Similarity	NPD3617	Approved
0.7632	Intermediate Similarity	NPD7101	Approved
0.7632	Intermediate Similarity	NPD7100	Approved
0.7624	Intermediate Similarity	NPD5133	Approved
0.7607	Intermediate Similarity	NPD7492	Approved
0.76	Intermediate Similarity	NPD5692	Phase 3
0.7593	Intermediate Similarity	NPD6412	Phase 2
0.7589	Intermediate Similarity	NPD5167	Approved
0.7586	Intermediate Similarity	NPD5988	Approved
0.7576	Intermediate Similarity	NPD5737	Approved
0.7576	Intermediate Similarity	NPD6672	Approved
0.7553	Intermediate Similarity	NPD4195	Approved
0.7551	Intermediate Similarity	NPD7146	Approved
0.7551	Intermediate Similarity	NPD6409	Approved
0.7551	Intermediate Similarity	NPD6684	Approved
0.7551	Intermediate Similarity	NPD7521	Approved
0.7551	Intermediate Similarity	NPD7334	Approved
0.7551	Intermediate Similarity	NPD5330	Approved
0.7547	Intermediate Similarity	NPD5091	Approved
0.7544	Intermediate Similarity	NPD6335	Approved
0.7542	Intermediate Similarity	NPD6616	Approved
0.7525	Intermediate Similarity	NPD5694	Approved
0.7523	Intermediate Similarity	NPD5168	Approved
0.7521	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD5983	Phase 2
0.7479	Intermediate Similarity	NPD7078	Approved
0.7478	Intermediate Similarity	NPD4522	Approved
0.7456	Intermediate Similarity	NPD6317	Approved
0.7451	Intermediate Similarity	NPD6399	Phase 3
0.7426	Intermediate Similarity	NPD4096	Approved
0.7417	Intermediate Similarity	NPD7736	Approved
0.7411	Intermediate Similarity	NPD6053	Discontinued
0.74	Intermediate Similarity	NPD6903	Approved
0.74	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4692	Approved
0.7396	Intermediate Similarity	NPD4139	Approved
0.7395	Intermediate Similarity	NPD6336	Discontinued
0.7391	Intermediate Similarity	NPD6313	Approved
0.7391	Intermediate Similarity	NPD6314	Approved
0.7374	Intermediate Similarity	NPD6098	Approved
0.7353	Intermediate Similarity	NPD5693	Phase 1
0.735	Intermediate Similarity	NPD6908	Approved
0.735	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6909	Approved
0.7333	Intermediate Similarity	NPD8293	Discontinued
0.7308	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5207	Approved
0.7228	Intermediate Similarity	NPD4518	Approved
0.7217	Intermediate Similarity	NPD6868	Approved
0.7184	Intermediate Similarity	NPD7515	Phase 2
0.7172	Intermediate Similarity	NPD3668	Phase 3
0.7157	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5654	Approved
0.7131	Intermediate Similarity	NPD6033	Approved
0.7103	Intermediate Similarity	NPD7638	Approved
0.7059	Intermediate Similarity	NPD5208	Approved
0.7053	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5282	Discontinued
0.7037	Intermediate Similarity	NPD7639	Approved
0.7037	Intermediate Similarity	NPD7640	Approved
0.7021	Intermediate Similarity	NPD5733	Approved
0.7009	Intermediate Similarity	NPD7115	Discovery
0.7009	Intermediate Similarity	NPD5959	Approved
0.6989	Remote Similarity	NPD4243	Approved
0.6964	Remote Similarity	NPD6614	Approved
0.6961	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6942	Approved
0.6947	Remote Similarity	NPD7339	Approved
0.6939	Remote Similarity	NPD7525	Registered
0.6939	Remote Similarity	NPD5368	Approved
0.6887	Remote Similarity	NPD6001	Approved
0.6887	Remote Similarity	NPD7748	Approved
0.6882	Remote Similarity	NPD4747	Approved
0.6882	Remote Similarity	NPD4691	Approved
0.688	Remote Similarity	NPD5956	Approved
0.6863	Remote Similarity	NPD4623	Approved
0.6863	Remote Similarity	NPD4519	Discontinued
0.6857	Remote Similarity	NPD6411	Approved
0.6852	Remote Similarity	NPD7902	Approved
0.6842	Remote Similarity	NPD4785	Approved
0.6842	Remote Similarity	NPD4784	Approved
0.6842	Remote Similarity	NPD4687	Approved
0.6829	Remote Similarity	NPD7507	Approved
0.6809	Remote Similarity	NPD5276	Approved
0.68	Remote Similarity	NPD6435	Approved
0.6774	Remote Similarity	NPD4137	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