NPASS Compound

Structure

NPC218383 OpenBabel07101718232D 36 39 0 0 1 0 0 0 0 0999 V2000 1.5180 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1293 -6.3916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 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 -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 3.8855 -1.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5398 -5.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 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 0.2308 -4.6974 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 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 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 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 -0.7473 -4.4895 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 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9074 -1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 6 30 1 0 0 0 0 8 36 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 10 21 2 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 23 1 0 0 0 0 17 31 1 0 0 0 0 18 22 1 0 0 0 0 19 9 1 6 0 0 0 19 26 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 31 1 0 0 0 0 22 32 1 1 0 0 0 23 26 1 0 0 0 0 23 33 1 6 0 0 0 24 28 1 0 0 0 0 24 29 1 6 0 0 0 25 28 1 0 0 0 0 25 34 2 0 0 0 0 26 30 1 1 0 0 0 27 35 2 0 0 0 0 27 36 1 0 0 0 0 29 5 1 6 0 0 0 30 31 1 1 0 0 0 31 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.35
Volume:	543.911
LogP:	4.768
LogD:	4.125
LogS:	-4.775
# Rotatable Bonds:	7
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	5.11
Fsp3:	0.806
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:	-4.958
MDCK Permeability:	1.7762265997589566e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.736
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.909
Plasma Protein Binding (PPB):	69.3185806274414%
Volume Distribution (VD):	1.263
Pgp-substrate:	22.668718338012695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.725
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.153
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.779

ADMET: Excretion

Clearance (CL):	8.633
Half-life (T1/2):	0.126

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.074
Carcinogencity:	0.309
Eye Corrosion:	0.007
Eye Irritation:	0.019
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC218383

Natural Product ID:	NPC218383
*Common Name:**	Meliastatin 4
IUPAC Name:	methyl (2R,5S)-5-hydroxy-2-[(5R,9R,10R,13S,14S,16S,17S)-16-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-6-enoate
Synonyms:	Meliastatin 4
Standard InCHIKey:	VQEYVSAEWJJGDI-DAODMKAJSA-N
Standard InCHI:	InChI=1S/C31H48O5/c1-18(2)22(32)11-9-19(27(35)36-8)26-23(33)17-31(7)21-10-12-24-28(3,4)25(34)14-15-29(24,5)20(21)13-16-30(26,31)6/h10,19-20,22-24,26,32-33H,1,9,11-17H2,2-8H3/t19-,20+,22+,23+,24+,26-,29-,30+,31-/m1/s1
SMILES:	C=C(C)[C@H](CC[C@H]([C@@H]1[C@H](C[C@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)[C@H]3CC[C@@]12C)O)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464451
PubChem CID:	11145528
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO18596	Melia dubia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502333]
NPO18596	Melia dubia	Species	Meliaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.0	ug ml-1	PMID[476988]

☑ 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 NPC218383 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	1137
0.2-0.3	4615
0.3-0.4	10450
0.4-0.5	10950
0.5-0.6	5699
0.6-0.7	6283
0.7-0.8	2978
0.8-0.85	324
0.85-0.9	73
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9278	High Similarity	NPC140723
0.9239	High Similarity	NPC154101
0.9158	High Similarity	NPC107243
0.9072	High Similarity	NPC474327
0.9062	High Similarity	NPC153792
0.9062	High Similarity	NPC271387
0.8958	High Similarity	NPC57416
0.8958	High Similarity	NPC475894
0.8947	High Similarity	NPC469599
0.8936	High Similarity	NPC243866
0.8936	High Similarity	NPC206810
0.89	High Similarity	NPC278628
0.89	High Similarity	NPC231530
0.89	High Similarity	NPC196528
0.8889	High Similarity	NPC236390
0.8854	High Similarity	NPC155676
0.8854	High Similarity	NPC42042
0.8846	High Similarity	NPC962
0.8817	High Similarity	NPC54689
0.88	High Similarity	NPC29705
0.8788	High Similarity	NPC195290
0.8788	High Similarity	NPC204450
0.8737	High Similarity	NPC152897
0.8737	High Similarity	NPC470376
0.8737	High Similarity	NPC470375
0.8737	High Similarity	NPC66429
0.8725	High Similarity	NPC94529
0.871	High Similarity	NPC294480
0.8696	High Similarity	NPC469994
0.8687	High Similarity	NPC121218
0.8687	High Similarity	NPC253886
0.8679	High Similarity	NPC266728
0.8679	High Similarity	NPC49492
0.8673	High Similarity	NPC197386
0.8673	High Similarity	NPC477854
0.8667	High Similarity	NPC250109
0.866	High Similarity	NPC49371
0.866	High Similarity	NPC173272
0.8654	High Similarity	NPC214797
0.8654	High Similarity	NPC118860
0.8654	High Similarity	NPC231589
0.8641	High Similarity	NPC258543
0.8641	High Similarity	NPC241927
0.8617	High Similarity	NPC477943
0.8617	High Similarity	NPC155479
0.8614	High Similarity	NPC28656
0.8602	High Similarity	NPC317590
0.8602	High Similarity	NPC312215
0.86	High Similarity	NPC473928
0.86	High Similarity	NPC22388
0.86	High Similarity	NPC136289
0.8587	High Similarity	NPC474218
0.8586	High Similarity	NPC167974
0.8586	High Similarity	NPC476274
0.8586	High Similarity	NPC154072
0.8586	High Similarity	NPC205899
0.8571	High Similarity	NPC190554
0.8571	High Similarity	NPC170487
0.8571	High Similarity	NPC18319
0.8558	High Similarity	NPC197428
0.8557	High Similarity	NPC263347
0.8557	High Similarity	NPC48330
0.8542	High Similarity	NPC470254
0.8529	High Similarity	NPC214264
0.8529	High Similarity	NPC96377
0.8529	High Similarity	NPC171137
0.8529	High Similarity	NPC152695
0.8529	High Similarity	NPC85829
0.8529	High Similarity	NPC48733
0.8529	High Similarity	NPC50692
0.8529	High Similarity	NPC260268
0.8529	High Similarity	NPC319077
0.8529	High Similarity	NPC476027
0.8529	High Similarity	NPC97202
0.8529	High Similarity	NPC49958
0.8529	High Similarity	NPC296945
0.8529	High Similarity	NPC302607
0.8529	High Similarity	NPC202167
0.8529	High Similarity	NPC150531
0.8515	High Similarity	NPC55872
0.8511	High Similarity	NPC183546
0.85	High Similarity	NPC476240
0.85	High Similarity	NPC224720
0.85	High Similarity	NPC81530
0.85	High Similarity	NPC472924
0.85	High Similarity	NPC476223
0.8495	Intermediate Similarity	NPC212843
0.8491	Intermediate Similarity	NPC52634
0.8491	Intermediate Similarity	NPC202889
0.8485	Intermediate Similarity	NPC48647
0.8485	Intermediate Similarity	NPC10364
0.8485	Intermediate Similarity	NPC186810
0.8478	Intermediate Similarity	NPC165064
0.8478	Intermediate Similarity	NPC82902
0.8469	Intermediate Similarity	NPC477853
0.8469	Intermediate Similarity	NPC328371
0.8462	Intermediate Similarity	NPC304495
0.8454	Intermediate Similarity	NPC111015
0.8454	Intermediate Similarity	NPC7165
0.8447	Intermediate Similarity	NPC220229
0.8447	Intermediate Similarity	NPC475060
0.8447	Intermediate Similarity	NPC83744
0.8447	Intermediate Similarity	NPC59530
0.844	Intermediate Similarity	NPC475041
0.8438	Intermediate Similarity	NPC45269
0.8438	Intermediate Similarity	NPC23434
0.8438	Intermediate Similarity	NPC107690
0.8431	Intermediate Similarity	NPC96268
0.8431	Intermediate Similarity	NPC235889
0.8431	Intermediate Similarity	NPC477812
0.8431	Intermediate Similarity	NPC204833
0.8431	Intermediate Similarity	NPC209502
0.8431	Intermediate Similarity	NPC47281
0.8431	Intermediate Similarity	NPC255309
0.8421	Intermediate Similarity	NPC2983
0.8421	Intermediate Similarity	NPC476733
0.8421	Intermediate Similarity	NPC215029
0.8416	Intermediate Similarity	NPC56498
0.8416	Intermediate Similarity	NPC170615
0.8411	Intermediate Similarity	NPC471398
0.8404	Intermediate Similarity	NPC96496
0.84	Intermediate Similarity	NPC83709
0.84	Intermediate Similarity	NPC51370
0.84	Intermediate Similarity	NPC287833
0.84	Intermediate Similarity	NPC15390
0.8396	Intermediate Similarity	NPC280782
0.8396	Intermediate Similarity	NPC71348
0.8387	Intermediate Similarity	NPC471224
0.8381	Intermediate Similarity	NPC76084
0.8367	Intermediate Similarity	NPC45324
0.8367	Intermediate Similarity	NPC472932
0.8367	Intermediate Similarity	NPC162001
0.8367	Intermediate Similarity	NPC174948
0.8367	Intermediate Similarity	NPC69548
0.8367	Intermediate Similarity	NPC184848
0.8367	Intermediate Similarity	NPC318282
0.8367	Intermediate Similarity	NPC469995
0.8367	Intermediate Similarity	NPC222845
0.8367	Intermediate Similarity	NPC173875
0.8365	Intermediate Similarity	NPC329417
0.8365	Intermediate Similarity	NPC217201
0.8364	Intermediate Similarity	NPC109973
0.8351	Intermediate Similarity	NPC25750
0.8351	Intermediate Similarity	NPC107674
0.8351	Intermediate Similarity	NPC170220
0.8351	Intermediate Similarity	NPC141497
0.8351	Intermediate Similarity	NPC477855
0.835	Intermediate Similarity	NPC50535
0.835	Intermediate Similarity	NPC149047
0.835	Intermediate Similarity	NPC37600
0.835	Intermediate Similarity	NPC181265
0.8333	Intermediate Similarity	NPC469985
0.8333	Intermediate Similarity	NPC289213
0.8333	Intermediate Similarity	NPC474775
0.8333	Intermediate Similarity	NPC148458
0.8333	Intermediate Similarity	NPC171441
0.8333	Intermediate Similarity	NPC46281
0.8333	Intermediate Similarity	NPC117185
0.8333	Intermediate Similarity	NPC123854
0.8333	Intermediate Similarity	NPC320026
0.8333	Intermediate Similarity	NPC232202
0.8333	Intermediate Similarity	NPC100313
0.8333	Intermediate Similarity	NPC270958
0.8333	Intermediate Similarity	NPC159442
0.8318	Intermediate Similarity	NPC317210
0.8317	Intermediate Similarity	NPC295276
0.8317	Intermediate Similarity	NPC39683
0.8316	Intermediate Similarity	NPC48866
0.8316	Intermediate Similarity	NPC247406
0.8316	Intermediate Similarity	NPC28227
0.83	Intermediate Similarity	NPC176845
0.83	Intermediate Similarity	NPC235464
0.83	Intermediate Similarity	NPC166745
0.83	Intermediate Similarity	NPC114274
0.83	Intermediate Similarity	NPC477813
0.8298	Intermediate Similarity	NPC322159
0.8298	Intermediate Similarity	NPC155011
0.8286	Intermediate Similarity	NPC11710
0.8283	Intermediate Similarity	NPC3772
0.8283	Intermediate Similarity	NPC29410
0.8283	Intermediate Similarity	NPC200054
0.8283	Intermediate Similarity	NPC111684
0.8283	Intermediate Similarity	NPC58052
0.8283	Intermediate Similarity	NPC125622
0.8283	Intermediate Similarity	NPC322063
0.828	Intermediate Similarity	NPC263974
0.8269	Intermediate Similarity	NPC477916
0.8269	Intermediate Similarity	NPC230541
0.8265	Intermediate Similarity	NPC184870
0.8252	Intermediate Similarity	NPC149124
0.8252	Intermediate Similarity	NPC471293
0.8252	Intermediate Similarity	NPC75531
0.8252	Intermediate Similarity	NPC228669
0.8252	Intermediate Similarity	NPC310586
0.8252	Intermediate Similarity	NPC164835
0.8247	Intermediate Similarity	NPC86266
0.8247	Intermediate Similarity	NPC110657
0.8247	Intermediate Similarity	NPC297265
0.8247	Intermediate Similarity	NPC212301
0.8247	Intermediate Similarity	NPC150383

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 NPC218383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1448
0.2-0.3	3923
0.3-0.4	2409
0.4-0.5	673
0.5-0.6	185
0.6-0.7	173
0.7-0.8	139
0.8-0.85	51
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8542	High Similarity	NPD6399	Phase 3
0.835	Intermediate Similarity	NPD6675	Approved
0.835	Intermediate Similarity	NPD5739	Approved
0.835	Intermediate Similarity	NPD7128	Approved
0.835	Intermediate Similarity	NPD6402	Approved
0.8286	Intermediate Similarity	NPD6372	Approved
0.8286	Intermediate Similarity	NPD6373	Approved
0.82	Intermediate Similarity	NPD6084	Phase 2
0.82	Intermediate Similarity	NPD6083	Phase 2
0.819	Intermediate Similarity	NPD7320	Approved
0.819	Intermediate Similarity	NPD6899	Approved
0.819	Intermediate Similarity	NPD6881	Approved
0.8173	Intermediate Similarity	NPD6008	Approved
0.8148	Intermediate Similarity	NPD4632	Approved
0.8131	Intermediate Similarity	NPD6649	Approved
0.8131	Intermediate Similarity	NPD6650	Approved
0.8105	Intermediate Similarity	NPD7146	Approved
0.8105	Intermediate Similarity	NPD7334	Approved
0.8105	Intermediate Similarity	NPD5330	Approved
0.8105	Intermediate Similarity	NPD7521	Approved
0.8105	Intermediate Similarity	NPD6409	Approved
0.8105	Intermediate Similarity	NPD6684	Approved
0.8095	Intermediate Similarity	NPD5701	Approved
0.8095	Intermediate Similarity	NPD5697	Approved
0.8085	Intermediate Similarity	NPD3133	Approved
0.8085	Intermediate Similarity	NPD4786	Approved
0.8085	Intermediate Similarity	NPD3665	Phase 1
0.8085	Intermediate Similarity	NPD3666	Approved
0.8058	Intermediate Similarity	NPD5211	Phase 2
0.8041	Intermediate Similarity	NPD5328	Approved
0.8039	Intermediate Similarity	NPD7640	Approved
0.8039	Intermediate Similarity	NPD7639	Approved
0.8037	Intermediate Similarity	NPD7290	Approved
0.8037	Intermediate Similarity	NPD7102	Approved
0.8037	Intermediate Similarity	NPD6883	Approved
0.802	Intermediate Similarity	NPD4755	Approved
0.8019	Intermediate Similarity	NPD6011	Approved
0.7963	Intermediate Similarity	NPD6617	Approved
0.7963	Intermediate Similarity	NPD6869	Approved
0.7963	Intermediate Similarity	NPD6847	Approved
0.7963	Intermediate Similarity	NPD8130	Phase 1
0.7963	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD6012	Approved
0.7944	Intermediate Similarity	NPD6014	Approved
0.7944	Intermediate Similarity	NPD6013	Approved
0.7941	Intermediate Similarity	NPD7638	Approved
0.7941	Intermediate Similarity	NPD5696	Approved
0.7938	Intermediate Similarity	NPD6903	Approved
0.7938	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD6009	Approved
0.7925	Intermediate Similarity	NPD6412	Phase 2
0.7905	Intermediate Similarity	NPD5141	Approved
0.789	Intermediate Similarity	NPD6882	Approved
0.789	Intermediate Similarity	NPD8297	Approved
0.7879	Intermediate Similarity	NPD5281	Approved
0.7879	Intermediate Similarity	NPD5284	Approved
0.7879	Intermediate Similarity	NPD6079	Approved
0.7872	Intermediate Similarity	NPD3667	Approved
0.7864	Intermediate Similarity	NPD5286	Approved
0.7864	Intermediate Similarity	NPD4700	Approved
0.7864	Intermediate Similarity	NPD4696	Approved
0.7864	Intermediate Similarity	NPD5285	Approved
0.7857	Intermediate Similarity	NPD4753	Phase 2
0.7822	Intermediate Similarity	NPD5695	Phase 3
0.78	Intermediate Similarity	NPD4202	Approved
0.7788	Intermediate Similarity	NPD5223	Approved
0.7755	Intermediate Similarity	NPD6672	Approved
0.7755	Intermediate Similarity	NPD5737	Approved
0.7745	Intermediate Similarity	NPD4697	Phase 3
0.7732	Intermediate Similarity	NPD3618	Phase 1
0.7732	Intermediate Similarity	NPD6098	Approved
0.7727	Intermediate Similarity	NPD6053	Discontinued
0.7719	Intermediate Similarity	NPD6319	Approved
0.7714	Intermediate Similarity	NPD5225	Approved
0.7714	Intermediate Similarity	NPD5224	Approved
0.7714	Intermediate Similarity	NPD5226	Approved
0.7714	Intermediate Similarity	NPD4633	Approved
0.7684	Intermediate Similarity	NPD4221	Approved
0.7684	Intermediate Similarity	NPD4223	Phase 3
0.7677	Intermediate Similarity	NPD6080	Approved
0.7677	Intermediate Similarity	NPD6904	Approved
0.7677	Intermediate Similarity	NPD6673	Approved
0.7672	Intermediate Similarity	NPD7604	Phase 2
0.7652	Intermediate Similarity	NPD5983	Phase 2
0.7647	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4629	Approved
0.7647	Intermediate Similarity	NPD5210	Approved
0.7642	Intermediate Similarity	NPD5174	Approved
0.7642	Intermediate Similarity	NPD4754	Approved
0.7642	Intermediate Similarity	NPD5175	Approved
0.7629	Intermediate Similarity	NPD5329	Approved
0.7607	Intermediate Similarity	NPD7492	Approved
0.7573	Intermediate Similarity	NPD5221	Approved
0.7573	Intermediate Similarity	NPD5222	Approved
0.7573	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD6059	Approved
0.7565	Intermediate Similarity	NPD6054	Approved
0.7551	Intermediate Similarity	NPD5786	Approved
0.7545	Intermediate Similarity	NPD4634	Approved
0.7544	Intermediate Similarity	NPD6335	Approved
0.7542	Intermediate Similarity	NPD6616	Approved
0.7542	Intermediate Similarity	NPD6336	Discontinued
0.7526	Intermediate Similarity	NPD4197	Approved
0.7525	Intermediate Similarity	NPD8034	Phase 2
0.7525	Intermediate Similarity	NPD5693	Phase 1
0.7525	Intermediate Similarity	NPD7515	Phase 2
0.7525	Intermediate Similarity	NPD8035	Phase 2
0.7522	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD4767	Approved
0.75	Intermediate Similarity	NPD6435	Approved
0.75	Intermediate Similarity	NPD4768	Approved
0.7479	Intermediate Similarity	NPD7078	Approved
0.7479	Intermediate Similarity	NPD8293	Discontinued
0.7478	Intermediate Similarity	NPD7101	Approved
0.7478	Intermediate Similarity	NPD7100	Approved
0.7474	Intermediate Similarity	NPD5368	Approved
0.7456	Intermediate Similarity	NPD6317	Approved
0.7449	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6370	Approved
0.7423	Intermediate Similarity	NPD5362	Discontinued
0.7423	Intermediate Similarity	NPD4788	Approved
0.7417	Intermediate Similarity	NPD7736	Approved
0.74	Intermediate Similarity	NPD5208	Approved
0.7395	Intermediate Similarity	NPD7507	Approved
0.7391	Intermediate Similarity	NPD6313	Approved
0.7391	Intermediate Similarity	NPD6314	Approved
0.7383	Intermediate Similarity	NPD7632	Discontinued
0.7379	Intermediate Similarity	NPD7748	Approved
0.7374	Intermediate Similarity	NPD4138	Approved
0.7374	Intermediate Similarity	NPD5205	Approved
0.7374	Intermediate Similarity	NPD5279	Phase 3
0.7374	Intermediate Similarity	NPD4690	Approved
0.7374	Intermediate Similarity	NPD4693	Phase 3
0.7374	Intermediate Similarity	NPD4688	Approved
0.7374	Intermediate Similarity	NPD4689	Approved
0.7364	Intermediate Similarity	NPD4730	Approved
0.7364	Intermediate Similarity	NPD4729	Approved
0.7364	Intermediate Similarity	NPD5128	Approved
0.7353	Intermediate Similarity	NPD7637	Suspended
0.7353	Intermediate Similarity	NPD6050	Approved
0.735	Intermediate Similarity	NPD6908	Approved
0.735	Intermediate Similarity	NPD6015	Approved
0.735	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6016	Approved
0.735	Intermediate Similarity	NPD6909	Approved
0.7347	Intermediate Similarity	NPD3668	Phase 3
0.7327	Intermediate Similarity	NPD6051	Approved
0.732	Intermediate Similarity	NPD4270	Approved
0.732	Intermediate Similarity	NPD4269	Approved
0.7304	Intermediate Similarity	NPD7115	Discovery
0.73	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5988	Approved
0.7282	Intermediate Similarity	NPD5778	Approved
0.7282	Intermediate Similarity	NPD5779	Approved
0.7255	Intermediate Similarity	NPD5207	Approved
0.7255	Intermediate Similarity	NPD5692	Phase 3
0.7255	Intermediate Similarity	NPD5785	Approved
0.7234	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5135	Approved
0.7232	Intermediate Similarity	NPD5250	Approved
0.7232	Intermediate Similarity	NPD5251	Approved
0.7232	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5169	Approved
0.7232	Intermediate Similarity	NPD5247	Approved
0.7232	Intermediate Similarity	NPD5249	Phase 3
0.7232	Intermediate Similarity	NPD5248	Approved
0.7217	Intermediate Similarity	NPD6868	Approved
0.7216	Intermediate Similarity	NPD5369	Approved
0.7213	Intermediate Similarity	NPD7319	Approved
0.7212	Intermediate Similarity	NPD7900	Approved
0.7212	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6001	Approved
0.7207	Intermediate Similarity	NPD6686	Approved
0.72	Intermediate Similarity	NPD5690	Phase 2
0.72	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5280	Approved
0.72	Intermediate Similarity	NPD4694	Approved
0.7184	Intermediate Similarity	NPD6411	Approved
0.7184	Intermediate Similarity	NPD5694	Approved
0.7172	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5215	Approved
0.7168	Intermediate Similarity	NPD5127	Approved
0.7168	Intermediate Similarity	NPD5216	Approved
0.7168	Intermediate Similarity	NPD5217	Approved
0.7131	Intermediate Similarity	NPD6033	Approved
0.7128	Intermediate Similarity	NPD7339	Approved
0.7128	Intermediate Similarity	NPD6942	Approved
0.7113	Intermediate Similarity	NPD4252	Approved
0.7113	Intermediate Similarity	NPD7525	Registered
0.71	Intermediate Similarity	NPD5363	Approved
0.7083	Intermediate Similarity	NPD6118	Approved
0.7083	Intermediate Similarity	NPD6114	Approved
0.7083	Intermediate Similarity	NPD6115	Approved
0.7083	Intermediate Similarity	NPD6697	Approved
0.7071	Intermediate Similarity	NPD6695	Phase 3
0.7054	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4692	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data